Sodium borohydride → Indopan, (+)-

HRID 1835116

反応式

HRID 1835116 の反応式
[NH2:1][C@@H:2]([CH3:14])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=O.[BH4-].[Na+]>C(#N)C.C(O)(C)C>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH2:3][C@@H:2]([NH2:1])[CH3:14])=[CH:6]1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 12993396(S)-2-amino-1-(1H-indol-3-yl)-propan-1-one

生成物 1

HCID 854157Indopan, (+)-

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6342Acetonitrile溶媒

実験手順

A solution of (S)-2-amino-1-(1H-indol-3-yl)-propan-1-one (0.47 g, 2.5 mmol, 1.0 eq.) in acetonitrile and isopropanol is treated portionwise with NaBH4 (285 mg, 7.49 mmol, 3.0 equiv.), heated at reflux temperature for 24 h, stirred at room temperature under N2 for 36 h, quenched with methanol, concentrated and partitioned between water and EtOAc. The EtOAc phase is dried over MgSO4 and concentrated in vacuo to afford the title product as a brown oil, identified by HPLC and mass spectral analyses.

後処理

  1. temperatureheated
  2. temperatureat reflux temperature for 24 h
  3. customquenched with methanol
  4. concentrationconcentrated
  5. custompartitioned between water and EtOAc
  6. dry with materialThe EtOAc phase is dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-00f191d7c9be496b9dba3aa8cf8d939c
出典データセット
uspto-grants-2004_08
特許番号
US06770642B2

関連ノート

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