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molecular formula C6H12O B105226 1-Methylcyclopentanol CAS No. 1462-03-9

1-Methylcyclopentanol

Cat. No. B105226
M. Wt: 100.16 g/mol
InChI Key: CAKWRXVKWGUISE-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08232287B2

Procedure details

Trifluoroacetic acid (2 mL) was added to a dichloromethane (10 mL) solution of the tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate (430 mg, 0.881 mmol) produced in Example 1, and the mixture was stirred at room temperature for 2 hours. From the reaction solution, the solvent was distilled off under reduced pressure. The same reaction as in the method described in Example 102 was performed using a portion (201 mg) of the obtained residue and, instead of 1-methylcyclopentanol, 2-methyl-2-butanol to obtain the title compound as white powder (50.4 mg, yield: 19%).
Quantity
2 mL
Type
reactant
Reaction Step One
Name
tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate
Quantity
430 mg
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
[Compound]
Name
obtained residue
Quantity
201 mg
Type
reactant
Reaction Step Two
Yield
19%

Identifiers

REACTION_CXSMILES
F[C:2](F)(F)C(O)=O.[CH3:8][S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[N:26]=[CH:25][N:24]=[C:23]([O:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)[CH:22]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]>ClCCl>[CH3:2][C:28]1([OH:27])[CH2:29][CH2:30][CH2:32][CH2:33]1.[CH3:39][C:37]([OH:36])([CH2:40][CH3:2])[CH3:38].[CH3:8][S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[N:26]=[CH:25][N:24]=[C:23]([O:27][CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH2:38][CH3:2])=[O:35])[CH2:32][CH2:33]3)[CH:22]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]

Inputs

Step One
Name
Quantity
2 mL
Type
reactant
Smiles
FC(C(=O)O)(F)F
Name
tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate
Quantity
430 mg
Type
reactant
Smiles
CS(=O)(=O)C=1C=C2CCN(C2=CC1)C1=CC(=NC=N1)OC1CCN(CC1)C(=O)OC(C)(C)C
Name
Quantity
10 mL
Type
solvent
Smiles
ClCCl
Step Two
Name
obtained residue
Quantity
201 mg
Type
reactant
Smiles

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
the mixture was stirred at room temperature for 2 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

DISTILLATION
Type
DISTILLATION
Details
From the reaction solution, the solvent was distilled off under reduced pressure
CUSTOM
Type
CUSTOM
Details
The same reaction as in the method

Outcomes

Product
Details
Reaction Time
2 h
Name
Type
product
Smiles
CC1(CCCC1)O
Name
Type
product
Smiles
CC(C)(CC)O
Name
Type
product
Smiles
CS(=O)(=O)C=1C=C2CCN(C2=CC1)C1=CC(=NC=N1)OC1CCN(CC1)C(=O)OC(CC)(C)C
Measurements
Type Value Analysis
AMOUNT: MASS 50.4 mg
YIELD: PERCENTYIELD 19%

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
US08232287B2

Procedure details

Trifluoroacetic acid (2 mL) was added to a dichloromethane (10 mL) solution of the tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate (430 mg, 0.881 mmol) produced in Example 1, and the mixture was stirred at room temperature for 2 hours. From the reaction solution, the solvent was distilled off under reduced pressure. The same reaction as in the method described in Example 102 was performed using a portion (201 mg) of the obtained residue and, instead of 1-methylcyclopentanol, 2-methyl-2-butanol to obtain the title compound as white powder (50.4 mg, yield: 19%).
Quantity
2 mL
Type
reactant
Reaction Step One
Name
tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate
Quantity
430 mg
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
[Compound]
Name
obtained residue
Quantity
201 mg
Type
reactant
Reaction Step Two
Yield
19%

Identifiers

REACTION_CXSMILES
F[C:2](F)(F)C(O)=O.[CH3:8][S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[N:26]=[CH:25][N:24]=[C:23]([O:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)[CH:22]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]>ClCCl>[CH3:2][C:28]1([OH:27])[CH2:29][CH2:30][CH2:32][CH2:33]1.[CH3:39][C:37]([OH:36])([CH2:40][CH3:2])[CH3:38].[CH3:8][S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[N:26]=[CH:25][N:24]=[C:23]([O:27][CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH2:38][CH3:2])=[O:35])[CH2:32][CH2:33]3)[CH:22]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]

Inputs

Step One
Name
Quantity
2 mL
Type
reactant
Smiles
FC(C(=O)O)(F)F
Name
tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate
Quantity
430 mg
Type
reactant
Smiles
CS(=O)(=O)C=1C=C2CCN(C2=CC1)C1=CC(=NC=N1)OC1CCN(CC1)C(=O)OC(C)(C)C
Name
Quantity
10 mL
Type
solvent
Smiles
ClCCl
Step Two
Name
obtained residue
Quantity
201 mg
Type
reactant
Smiles

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
the mixture was stirred at room temperature for 2 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

DISTILLATION
Type
DISTILLATION
Details
From the reaction solution, the solvent was distilled off under reduced pressure
CUSTOM
Type
CUSTOM
Details
The same reaction as in the method

Outcomes

Product
Details
Reaction Time
2 h
Name
Type
product
Smiles
CC1(CCCC1)O
Name
Type
product
Smiles
CC(C)(CC)O
Name
Type
product
Smiles
CS(=O)(=O)C=1C=C2CCN(C2=CC1)C1=CC(=NC=N1)OC1CCN(CC1)C(=O)OC(CC)(C)C
Measurements
Type Value Analysis
AMOUNT: MASS 50.4 mg
YIELD: PERCENTYIELD 19%

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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