Methanol → methyl (1R,3S)-3-aminocyclopentane-1-carboxylate hydrochloride
Reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[NH2:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A suspension of (1R,3S)-3-aminocyclopentanecarboxylic acid (500 mg, 3.8 mmol) in methanol (10 mL) was stirred at 0° C. and thionyl chloride (1.40 mL, 19.3 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The resulting clear solution was evaporated, azeotroped with methanol (2×5 mL), air-dried and the title compound obtained as a white powder (680 mg).
Workup
- temperatureto warm to room temperature
- stirringstirred overnight
- customThe resulting clear solution was evaporated
- customazeotroped with methanol (2×5 mL)
- customair-dried
Sources & evidence
- ORD record
- ord-ff8ad62118e64c688718a03c89790c93
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08435968B2
Reaction notes
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