Dichloromethane → tert-Butyl (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 1426370

반응식

HRID 1426370 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].ClCCl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][N:11]([C:16]([O:17][C:5]([CH3:8])([CH3:6])[CH3:4])=[O:19])[CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6344Dichloromethane2회HCID 10340Sodium CarbonateHCID 9855829(3S,4R)-4-(4-Fluorophenyl)-3-piperidinemethanol

생성물 1

HCID 10018204tert-Butyl (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate수율 184.7%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a mixture of [(3S,4R)-4-(4-fluorophenyl)piperidine-3-yl]methanol (3.0 g, 14 mmol), sodium carbonate (6.1 g, 57 mmol), dichloromethane (40 mL) and water (40 mL) was added di-tert-butyl Bicarbonate (3.8 g, 17 mmol) under ice cooling, followed by stirring at the same temperature for 30 minutes. The reaction mixture was added to a mixed solution of dichloromethane and water, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1) to give the title compound (4.0 g, 90% yield).

후처리

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1)

출처 및 근거

ORD 기록
ord-0eb7680ef5ee43f08cff9804d6073cc4
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933100B2

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