Sodium Hydroxide → (S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propylamine

HRID 1379966ノート

反応式

HRID 1379966 の反応式
[CH3:1][NH:2][C:3](=O)[C@@H:4]([N:12]([CH2:20][CH:21]=[CH2:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>ClCCl>[CH3:1][NH:2][CH2:3][C@@H:4]([N:12]([CH2:20][CH:21]=[CH2:22])[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 86750266(S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

生成物 1

HCID 67711663(S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propylamine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Dissolve (S)-N-methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide (0.31 g, 0.98 mmol) in dichloromethane (10 mL) and cool in a dry ice/acetone bath to -78° C. Add diisobutylaluminum hydride (1.96 mL, 1.5M in toluene, 2.94 mmol). Allow to warm slowly to ambient temperature and stir for 16 hours. Slowly add a 15% aqueous solution of sodium hydroxide (3.0 mL). Extract with dichloromethane, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound as a mixture which is taken on to the next step without further purification.

後処理

  1. temperatureAllow to warm slowly to ambient temperature
  2. extractionExtract with dichloromethane
  3. dry with materialdry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo

出典と根拠

ORDレコード
ord-58a860160cd84251ba259d3f8fcb0d57
出典データセット
uspto-grants-1997_09
特許番号
US05672602

反応ノート

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