Sodium hydride → Ethyl 3-(3,4-difluorobenzyl)-2-oxopiperidine-3-carboxylate

HRID 71144

반응식

HRID 71144 반응식
[O:1]=[C:2]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=1>CN(C=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>[F:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[F:23])[CH2:16][C:7]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:1]

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 977733-Carbethoxy-2-piperidoneHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

생성물 1

HCID 66607767Ethyl 3-(3,4-difluorobenzyl)-2-oxopiperidine-3-carboxylate

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

반응 조건

온도
0 °C

실험 절차

Under a nitrogen atmosphere, to a mixture of ethyl 2-oxopiperidine-3-carboxylate (2.0 g) in DMF (20 mL) was added sodium hydride (60%, 0.47 g) at 0° C., and the mixture was stirred at 0° C. for 30 min. 4-(Bromomethyl)-1,2-difluorobenzene (1.50 mL) was added to the reaction mixture, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and saturated aqueous ammonium chloride solution, the mixture was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.82 g).

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. washthe mixture was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-6984390e460d42cfaf5e95d0ceef91d0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822699B2

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