Methanol → N-[(1S)-1-(3-Fluorophenyl)-3-hydroxypropyl]acetamide

HRID 2105956Notes

Reaction equation

HRID 2105956 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]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 59985529Ethyl (3S)-3-(acetamido)-3-(3-fluorophenyl)propanoate

Product 1

HCID 59985487N-[(1S)-1-(3-Fluorophenyl)-3-hydroxypropyl]acetamideYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

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). LRMS (electrospray): m/z [M+H]+ 212.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for one hour
  3. temperatureto cool to room temperature
  4. extractionThe solution was extracted with ethyl acetate (3×30 ml)
  5. dry with materialthe combined organic extracts dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-5302d83a68f3495f92fc7298bdbe64c1
Source dataset
uspto-grants-2009_08
Patent number
US07579471B2

Reaction notes

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