Water → ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate

HRID 590978

반응식

HRID 590978 반응식
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:11]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>O1CCCC1.CO>[OH:25][CH:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH3:9])[C:11]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

참가 물질

6

반응물 3

HCID 962WaterHCID 70855253ethyl (1-methyl-2-phenyl-1H-indol-3-yl)-oxo-acetateHCID 131720822Sodium tetraborohydride

생성물 1

HCID 70855247ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate수율 69.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

At 0° C., sodium tetraborohydride (78 mg, 2 mmol) was added to a solution of ethyl (1-methyl-2-phenyl-1H-indol-3-yl)-oxo-acetate (8a) (630 mg, 2.05 mmol) in a mixture of tetrahydrofuran (10 mL) and methanol (15 mL). The mixture was stirred at room temperature for 2 hours and then hydrolyzed with water. Methanol and tetrahydrofuran were removed under reduced pressure and the residue was diluted with dichloromethane. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to afford the desired alcohol (8b) (440 mg, 1.42 mmol, 69%).

후처리

  1. customMethanol and tetrahydrofuran were removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (dichloromethane)

출처 및 근거

ORD 기록
ord-28973bfa09cd4955b5bf124020eadc92
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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