Methanol → N-[(1S)-1-(3-Fluorophenyl)-3-hydroxypropyl]acetamide
Reaction equation
[C:1]([NH:4][C@H:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH2:6][C:7](OCC)=[O:8])(=[O:3])[CH3:2].[BH4-].[Na+].CO.[OH-].[Na+]>C1COCC1.O>[F:18][C:14]1[CH:13]=[C:12]([C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7][OH:8])[CH:17]=[CH:16][CH:15]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A stirred suspension of ethyl (3S)-3-(acetylamino)-3-(3-fluorophenyl)propanoate (2.5 g, 9.9 mmol) and sodium borohydride (0.76 g, 20 mmol) in THF (20 ml) was heated at 50° C. under a nitrogen atmosphere. Methanol (1.8 ml) was then carefully added dropwise and the reaction mixture heated under reflux for one hour. The reaction was allowed to cool to room temperature then water (10 ml) and aqueous sodium hydroxide solution (1.5 g NaOH in 4 ml water) carefully added dropwise. The solution was extracted with ethyl acetate (3×30 ml) and the combined organic extracts dried (MgSO4) and evaporated to give the title compound as a white solid (2.08 g).
Workup
- temperaturethe reaction mixture heated
- temperatureunder reflux for one hour
- temperatureto cool to room temperature
- extractionThe solution was extracted with ethyl acetate (3×30 ml)
- dry with materialthe combined organic extracts dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-8780967861a240098a05d8f2fa23db4a
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217721B2
Reaction notes
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