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molecular formula C12H27OP B122868 Tributylphosphine oxide CAS No. 814-29-9

Tributylphosphine oxide

Cat. No. B122868
M. Wt: 218.32 g/mol
InChI Key: MNZAKDODWSQONA-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08552181B2

Procedure details

A solution of (5)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate (0.740 g, 1.7 mmol) and 1H-imidazole (0.35 g, 5.1 mmol) in 3 mL toluen was thoroughly degassed and treated with tributylphosphine (0.42 ml, 1.7 mmol). The reaction mixture was heated to reflux and allowed to stir for 3 hours. NaH (60% dispersion in mineral oil) (0.069 g, 2.9 mmol) was added and the reaction mixture was allowed to stir at 110° C. overnight. The reaction mixture was quenched with saturated NH4Cl solution and diluted with EtOAc. The reaction mixture was washed with water then brine. The organics were dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatography gave tert-butyl (2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(1H-imidazol-1-yl)butan-2-ylcarbamate with tributylphosphine oxide as the major impurity. This material was used without further purification.
Name
(5)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate
Quantity
0.74 g
Type
reactant
Reaction Step One
Quantity
0.35 g
Type
reactant
Reaction Step One
Quantity
3 mL
Type
solvent
Reaction Step One
Quantity
0.42 mL
Type
reactant
Reaction Step Two
Name
Quantity
0.069 g
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Si:1]([O:8][C@@H:9]([CH:19]1[CH2:21][N@@:20]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.[CH2:34]([P:38]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH3:37].[H-].[Na+]>C1(C)C=CC=CC=1>[Si:1]([O:8][C@H:9]([CH2:10][O:11][Si:12]([C:15]([CH3:16])([CH3:18])[CH3:17])([CH3:13])[CH3:14])[C@@H:19]([NH:20][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:21][N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2].[CH2:43]([P:38](=[O:8])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:39][CH2:40][CH2:41][CH3:42])[CH2:44][CH2:45][CH3:46] |f:3.4|

Inputs

Step One
Name
(5)-tert-butyl 2-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)aziridine-1-carboxylate
Quantity
0.74 g
Type
reactant
Smiles
[Si](C)(C)(C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)C1[N@](C1)C(=O)OC(C)(C)C
Name
Quantity
0.35 g
Type
reactant
Smiles
N1C=NC=C1
Name
Quantity
3 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Step Two
Name
Quantity
0.42 mL
Type
reactant
Smiles
C(CCC)P(CCCC)CCCC
Step Three
Name
Quantity
0.069 g
Type
reactant
Smiles
[H-].[Na+]

Conditions

Stirring
Type
CUSTOM
Details
to stir for 3 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
TEMPERATURE
Type
TEMPERATURE
Details
to reflux
STIRRING
Type
STIRRING
Details
to stir at 110° C. overnight
Duration
8 (± 8) h
CUSTOM
Type
CUSTOM
Details
The reaction mixture was quenched with saturated NH4Cl solution
ADDITION
Type
ADDITION
Details
diluted with EtOAc
WASH
Type
WASH
Details
The reaction mixture was washed with water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The organics were dried over MgSO4
CONCENTRATION
Type
CONCENTRATION
Details
concentrated in vacuo
CUSTOM
Type
CUSTOM
Details
Purification of the crude residue by column chromatography

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
[Si](C)(C)(C(C)(C)C)O[C@@H]([C@H](CN1C=NC=C1)NC(OC(C)(C)C)=O)CO[Si](C)(C)C(C)(C)C
Name
Type
product
Smiles
C(CCC)P(CCCC)(CCCC)=O

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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