Methanol → 4-benzyloxy-1-(4-{[(3S)-1-cyclopentyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one

HRID 15036

반응식

HRID 15036 반응식
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C@H:30]3[CH2:34][CH2:33][NH:32][CH2:31]3)=[CH:25][CH:24]=2)[C:19](=[O:35])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C@H:30]3[CH2:34][CH2:33][N:32]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:31]3)=[CH:25][CH:24]=2)[C:19](=[O:35])[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 8452CyclopentanoneHCID 684307174-benzyloxy-1-{4-[(3S)-3-pyrrolidinyloxy]phenyl}-1H-pyridin-2-one

생성물 1

HCID 589648874-benzyloxy-1-(4-{[(3S)-1-cyclopentyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one수율 53%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Cyclopentanone (0.017 mL, 0.186 mmol) and a 0.3 mol Zn[B(CN)H3]2 methanol solution (0.4 mL, 0.12 mmol, prepared from ZnCl2 and NaB(CN)H3) were added to a methanol solution (1 mL) of 4-benzyloxy-1-{4-[(3S)-3-pyrrolidinyloxy]phenyl}-1H-pyridin-2-one (45 mg, 0.124 mmol) and sired at room temperature for an hour. Ethyl acetate was added to the reaction liquid, which was then washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous potassium carbonate. The solvent was concentrated under reduced pressure and the resulting residue was purified on silica gel chromatography (C-300; methanol:chloroform=1:10) to provide the title compound (28.2 mg, 53%).

후처리

  1. waitsired at room temperature for an hour
  2. washwas then washed with saturated aqueous sodium bicarbonate solution and saturated brine
  3. dry with materialdried over anhydrous potassium carbonate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe resulting residue was purified on silica gel chromatography (C-300; methanol:chloroform=1:10)

출처 및 근거

ORD 기록
ord-256b9f0733d545b8b8f0ddf87a008d52
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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