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molecular formula C17H21NO3 B192826 (+)-Galanthamine CAS No. 60384-53-4

(+)-Galanthamine

Cat. No. B192826
M. Wt: 287.35 g/mol
InChI Key: ASUTZQLVASHGKV-SUYBPPKGSA-N
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Patent
US06018043

Procedure details

Lithium aluminium hydride (1M in ether, 1.2 ml, 1.20 mmol) was placed in a two necked round bottom flask fitted with a reflux condenser and nitrogen inlet. (-)-N-methy-ephedrine (0.23 g, 1.26 mmol) in ether (1 ml) was added dropwise and the solution was heated at reflux for 1 hour then cooled to room temperature. N-Ethyl-2-aminopyridine (0.31g, 2.52 mmol) in ether (1 ml) was added and the bright yellow solution was heated under reflux for a further 1 hour. The solution was cooled to -78° C. and solid (+) narwedine (97% e.e) (0.10 g, 0.35 mmol) was added. The suspension was warmed to 0° C., stirred for 20 hours and then allowed to warm to room temperature over 1 hour. The reaction was quenched 2M potassium carbonate (10 ml). The mixture was extracted into ethyl acetate (2×10 ml) and then the combined organic layer was washed with water (5 ml) and brine (5 ml) and dried over magnesium sulphate. Filtration and evaporation gave an orange oil which was shown by NMR and GC-MS to contain galanthamine and epigalanthamine in a 1:1 mixture. Flash chromatography on silica in dichloromethane-methanol 10:1 yielded (+) galanthamine (98% e.e.) (30% yield) and (+)-epigalanthamine (95% e.e) (26% yield). ##STR3##
Name
dichloromethane methanol
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
1.2 mL
Type
reactant
Reaction Step Two
[Compound]
Name
(-)-N-methy-ephedrine
Quantity
0.23 g
Type
reactant
Reaction Step Three
Name
Quantity
1 mL
Type
solvent
Reaction Step Three
Quantity
0.31 g
Type
reactant
Reaction Step Four
Name
Quantity
1 mL
Type
solvent
Reaction Step Four
Quantity
0.1 g
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven

Identifiers

REACTION_CXSMILES
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(N1C=CC=CC1N)C.[CH3:16][N:17]1[CH2:34][C:32]2=[C:33]3[C:28](=[C:29]([O:35][CH3:36])[CH:30]=[CH:31]2)[O:27][C@H:26]2[C@@:20]3([CH:21]=[CH:22][C:23]([CH2:25]2)=[O:24])[CH2:19][CH2:18]1.CN1CC2C=CC(OC)=C3C=2[C@]2([C@@H](O3)C[C@@H](O)C=C2)CC1.CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1>CCOCC.ClCCl.CO>[CH3:16][N:17]1[CH2:34][C:32]2=[C:33]3[C:28](=[C:29]([O:35][CH3:36])[CH:30]=[CH:31]2)[O:27][C@H:26]2[C@@:20]3([CH:21]=[CH:22][C@@H:23]([OH:24])[CH2:25]2)[CH2:19][CH2:18]1 |f:0.1.2.3.4.5,11.12|

Inputs

Step One
Name
dichloromethane methanol
Quantity
0 (± 1) mol
Type
solvent
Smiles
ClCCl.CO
Step Two
Name
Quantity
1.2 mL
Type
reactant
Smiles
[H-].[Al+3].[Li+].[H-].[H-].[H-]
Step Three
Name
(-)-N-methy-ephedrine
Quantity
0.23 g
Type
reactant
Smiles
Name
Quantity
1 mL
Type
solvent
Smiles
CCOCC
Step Four
Name
Quantity
0.31 g
Type
reactant
Smiles
C(C)N1C(C=CC=C1)N
Name
Quantity
1 mL
Type
solvent
Smiles
CCOCC
Step Five
Name
Quantity
0.1 g
Type
reactant
Smiles
CN1CC[C@]23C=CC(=O)C[C@H]2OC4=C(C=CC(=C34)C1)OC
Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC=4C3=C(C=CC4OC)C1)O
Step Seven
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred for 20 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
fitted with a reflux condenser and nitrogen inlet
TEMPERATURE
Type
TEMPERATURE
Details
the solution was heated
TEMPERATURE
Type
TEMPERATURE
Details
at reflux for 1 hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
the bright yellow solution was heated
TEMPERATURE
Type
TEMPERATURE
Details
under reflux for a further 1 hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
The solution was cooled to -78° C.
TEMPERATURE
Type
TEMPERATURE
Details
The suspension was warmed to 0° C.
TEMPERATURE
Type
TEMPERATURE
Details
to warm to room temperature over 1 hour
Duration
1 h
CUSTOM
Type
CUSTOM
Details
The reaction was quenched 2M potassium carbonate (10 ml)
EXTRACTION
Type
EXTRACTION
Details
The mixture was extracted into ethyl acetate (2×10 ml)
WASH
Type
WASH
Details
the combined organic layer was washed with water (5 ml) and brine (5 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulphate
FILTRATION
Type
FILTRATION
Details
Filtration and evaporation
CUSTOM
Type
CUSTOM
Details
gave an orange oil which

Outcomes

Product
Details
Reaction Time
20 h
Name
Type
product
Smiles
CN1CC[C@]23C=C[C@H](C[C@H]2OC4=C(C=CC(=C34)C1)OC)O
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 30%
Name
Type
product
Smiles
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 26%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US06018043

Procedure details

Lithium aluminium hydride (1M in ether, 1.2 ml, 1.20 mmol) was placed in a two necked round bottom flask fitted with a reflux condenser and nitrogen inlet. (-)-N-methy-ephedrine (0.23 g, 1.26 mmol) in ether (1 ml) was added dropwise and the solution was heated at reflux for 1 hour then cooled to room temperature. N-Ethyl-2-aminopyridine (0.31g, 2.52 mmol) in ether (1 ml) was added and the bright yellow solution was heated under reflux for a further 1 hour. The solution was cooled to -78° C. and solid (+) narwedine (97% e.e) (0.10 g, 0.35 mmol) was added. The suspension was warmed to 0° C., stirred for 20 hours and then allowed to warm to room temperature over 1 hour. The reaction was quenched 2M potassium carbonate (10 ml). The mixture was extracted into ethyl acetate (2×10 ml) and then the combined organic layer was washed with water (5 ml) and brine (5 ml) and dried over magnesium sulphate. Filtration and evaporation gave an orange oil which was shown by NMR and GC-MS to contain galanthamine and epigalanthamine in a 1:1 mixture. Flash chromatography on silica in dichloromethane-methanol 10:1 yielded (+) galanthamine (98% e.e.) (30% yield) and (+)-epigalanthamine (95% e.e) (26% yield). ##STR3##
Name
dichloromethane methanol
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
1.2 mL
Type
reactant
Reaction Step Two
[Compound]
Name
(-)-N-methy-ephedrine
Quantity
0.23 g
Type
reactant
Reaction Step Three
Name
Quantity
1 mL
Type
solvent
Reaction Step Three
Quantity
0.31 g
Type
reactant
Reaction Step Four
Name
Quantity
1 mL
Type
solvent
Reaction Step Four
Quantity
0.1 g
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven

Identifiers

REACTION_CXSMILES
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(N1C=CC=CC1N)C.[CH3:16][N:17]1[CH2:34][C:32]2=[C:33]3[C:28](=[C:29]([O:35][CH3:36])[CH:30]=[CH:31]2)[O:27][C@H:26]2[C@@:20]3([CH:21]=[CH:22][C:23]([CH2:25]2)=[O:24])[CH2:19][CH2:18]1.CN1CC2C=CC(OC)=C3C=2[C@]2([C@@H](O3)C[C@@H](O)C=C2)CC1.CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1>CCOCC.ClCCl.CO>[CH3:16][N:17]1[CH2:34][C:32]2=[C:33]3[C:28](=[C:29]([O:35][CH3:36])[CH:30]=[CH:31]2)[O:27][C@H:26]2[C@@:20]3([CH:21]=[CH:22][C@@H:23]([OH:24])[CH2:25]2)[CH2:19][CH2:18]1 |f:0.1.2.3.4.5,11.12|

Inputs

Step One
Name
dichloromethane methanol
Quantity
0 (± 1) mol
Type
solvent
Smiles
ClCCl.CO
Step Two
Name
Quantity
1.2 mL
Type
reactant
Smiles
[H-].[Al+3].[Li+].[H-].[H-].[H-]
Step Three
Name
(-)-N-methy-ephedrine
Quantity
0.23 g
Type
reactant
Smiles
Name
Quantity
1 mL
Type
solvent
Smiles
CCOCC
Step Four
Name
Quantity
0.31 g
Type
reactant
Smiles
C(C)N1C(C=CC=C1)N
Name
Quantity
1 mL
Type
solvent
Smiles
CCOCC
Step Five
Name
Quantity
0.1 g
Type
reactant
Smiles
CN1CC[C@]23C=CC(=O)C[C@H]2OC4=C(C=CC(=C34)C1)OC
Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC=4C3=C(C=CC4OC)C1)O
Step Seven
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred for 20 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
fitted with a reflux condenser and nitrogen inlet
TEMPERATURE
Type
TEMPERATURE
Details
the solution was heated
TEMPERATURE
Type
TEMPERATURE
Details
at reflux for 1 hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
the bright yellow solution was heated
TEMPERATURE
Type
TEMPERATURE
Details
under reflux for a further 1 hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
The solution was cooled to -78° C.
TEMPERATURE
Type
TEMPERATURE
Details
The suspension was warmed to 0° C.
TEMPERATURE
Type
TEMPERATURE
Details
to warm to room temperature over 1 hour
Duration
1 h
CUSTOM
Type
CUSTOM
Details
The reaction was quenched 2M potassium carbonate (10 ml)
EXTRACTION
Type
EXTRACTION
Details
The mixture was extracted into ethyl acetate (2×10 ml)
WASH
Type
WASH
Details
the combined organic layer was washed with water (5 ml) and brine (5 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulphate
FILTRATION
Type
FILTRATION
Details
Filtration and evaporation
CUSTOM
Type
CUSTOM
Details
gave an orange oil which

Outcomes

Product
Details
Reaction Time
20 h
Name
Type
product
Smiles
CN1CC[C@]23C=C[C@H](C[C@H]2OC4=C(C=CC(=C34)C1)OC)O
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 30%
Name
Type
product
Smiles
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 26%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US06018043

Procedure details

Lithium aluminium hydride (1M in ether, 1.2 ml, 1.20 mmol) was placed in a two necked round bottom flask fitted with a reflux condenser and nitrogen inlet. (-)-N-methy-ephedrine (0.23 g, 1.26 mmol) in ether (1 ml) was added dropwise and the solution was heated at reflux for 1 hour then cooled to room temperature. N-Ethyl-2-aminopyridine (0.31g, 2.52 mmol) in ether (1 ml) was added and the bright yellow solution was heated under reflux for a further 1 hour. The solution was cooled to -78° C. and solid (+) narwedine (97% e.e) (0.10 g, 0.35 mmol) was added. The suspension was warmed to 0° C., stirred for 20 hours and then allowed to warm to room temperature over 1 hour. The reaction was quenched 2M potassium carbonate (10 ml). The mixture was extracted into ethyl acetate (2×10 ml) and then the combined organic layer was washed with water (5 ml) and brine (5 ml) and dried over magnesium sulphate. Filtration and evaporation gave an orange oil which was shown by NMR and GC-MS to contain galanthamine and epigalanthamine in a 1:1 mixture. Flash chromatography on silica in dichloromethane-methanol 10:1 yielded (+) galanthamine (98% e.e.) (30% yield) and (+)-epigalanthamine (95% e.e) (26% yield). ##STR3##
Name
dichloromethane methanol
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Quantity
1.2 mL
Type
reactant
Reaction Step Two
[Compound]
Name
(-)-N-methy-ephedrine
Quantity
0.23 g
Type
reactant
Reaction Step Three
Name
Quantity
1 mL
Type
solvent
Reaction Step Three
Quantity
0.31 g
Type
reactant
Reaction Step Four
Name
Quantity
1 mL
Type
solvent
Reaction Step Four
Quantity
0.1 g
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven

Identifiers

REACTION_CXSMILES
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(N1C=CC=CC1N)C.[CH3:16][N:17]1[CH2:34][C:32]2=[C:33]3[C:28](=[C:29]([O:35][CH3:36])[CH:30]=[CH:31]2)[O:27][C@H:26]2[C@@:20]3([CH:21]=[CH:22][C:23]([CH2:25]2)=[O:24])[CH2:19][CH2:18]1.CN1CC2C=CC(OC)=C3C=2[C@]2([C@@H](O3)C[C@@H](O)C=C2)CC1.CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1>CCOCC.ClCCl.CO>[CH3:16][N:17]1[CH2:34][C:32]2=[C:33]3[C:28](=[C:29]([O:35][CH3:36])[CH:30]=[CH:31]2)[O:27][C@H:26]2[C@@:20]3([CH:21]=[CH:22][C@@H:23]([OH:24])[CH2:25]2)[CH2:19][CH2:18]1 |f:0.1.2.3.4.5,11.12|

Inputs

Step One
Name
dichloromethane methanol
Quantity
0 (± 1) mol
Type
solvent
Smiles
ClCCl.CO
Step Two
Name
Quantity
1.2 mL
Type
reactant
Smiles
[H-].[Al+3].[Li+].[H-].[H-].[H-]
Step Three
Name
(-)-N-methy-ephedrine
Quantity
0.23 g
Type
reactant
Smiles
Name
Quantity
1 mL
Type
solvent
Smiles
CCOCC
Step Four
Name
Quantity
0.31 g
Type
reactant
Smiles
C(C)N1C(C=CC=C1)N
Name
Quantity
1 mL
Type
solvent
Smiles
CCOCC
Step Five
Name
Quantity
0.1 g
Type
reactant
Smiles
CN1CC[C@]23C=CC(=O)C[C@H]2OC4=C(C=CC(=C34)C1)OC
Step Six
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC=4C3=C(C=CC4OC)C1)O
Step Seven
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred for 20 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
fitted with a reflux condenser and nitrogen inlet
TEMPERATURE
Type
TEMPERATURE
Details
the solution was heated
TEMPERATURE
Type
TEMPERATURE
Details
at reflux for 1 hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
the bright yellow solution was heated
TEMPERATURE
Type
TEMPERATURE
Details
under reflux for a further 1 hour
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
The solution was cooled to -78° C.
TEMPERATURE
Type
TEMPERATURE
Details
The suspension was warmed to 0° C.
TEMPERATURE
Type
TEMPERATURE
Details
to warm to room temperature over 1 hour
Duration
1 h
CUSTOM
Type
CUSTOM
Details
The reaction was quenched 2M potassium carbonate (10 ml)
EXTRACTION
Type
EXTRACTION
Details
The mixture was extracted into ethyl acetate (2×10 ml)
WASH
Type
WASH
Details
the combined organic layer was washed with water (5 ml) and brine (5 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulphate
FILTRATION
Type
FILTRATION
Details
Filtration and evaporation
CUSTOM
Type
CUSTOM
Details
gave an orange oil which

Outcomes

Product
Details
Reaction Time
20 h
Name
Type
product
Smiles
CN1CC[C@]23C=C[C@H](C[C@H]2OC4=C(C=CC(=C34)C1)OC)O
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 30%
Name
Type
product
Smiles
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 26%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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