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

HRID 23933노트

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HRID 23933 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b938b617d55643e6a1c0f08442a3f1b6
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855724B2

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