Sodium Hydroxide → 3-[7-(1,3-Dimethyl-1H-pyrazol-5-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-1-butanol

HRID 1674496노트

반응식

HRID 1674496 반응식
[CH3:1][N:2]1[C:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:18])=[N:3]1.[OH:19][CH2:20][CH2:21][C:22](=O)[CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][N:13]([CH:22]([CH3:23])[CH2:21][CH2:20][OH:19])[CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:18])=[N:3]1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 1115094-Hydroxy-2-ButanoneHCID 5049666Sodium triacetoxyborohydrideHCID 251050497-(1,3-Dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine2회

생성물 1

HCID 598642713-[7-(1,3-Dimethyl-1H-pyrazol-5-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-1-butanol수율 38.5%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (0.5 g) (intermediate 3) in tetrahydrofuran (5 ml), at room temperature, 4-hydroxy-2-butanone (0.22 g), glacial acetic acid (0.12 ml) and sodium triacetoxyborohydride (0.53 g) were subsequently added. After stirring over night the mixture was made alkaline with 1N aqueous sodium hydroxide and extracted with dichloromethane. The organic phase was dried with sodium sulphate and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel with 70% cyclohexane-ethyl acetate to give the title compound (0.25 g) as a white solid.

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried with sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel with 70% cyclohexane-ethyl acetate

출처 및 근거

ORD 기록
ord-a6a99e3523224e038cfb9e8940c747d5
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003638B2

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