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

HRID 2105956ノート

反応式

HRID 2105956 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5302d83a68f3495f92fc7298bdbe64c1
出典データセット
uspto-grants-2009_08
特許番号
US07579471B2

反応ノート

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