Sodium borohydride → Indopan, (+)-

HRID 1793860

반응식

HRID 1793860 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 854157Indopan, (+)-

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c793f9490a5a4c95b768b947b315a2f1
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022701B2

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