Acetic Acid → trans-6-(2,5-Difluorophenyl)-1-benzyl-5-nitropiperidin-2-one

HRID 241573

반응식

HRID 241573 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.[N+:11]([CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=O)([O-:13])=[O:12].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+].C(O)(=O)C>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C@@H:4]1[N:28]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](=[O:19])[CH2:16][CH2:15][C@H:14]1[N+:11]([O-:13])=[O:12]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 25604Methyl 4-nitrobutyrateHCID 1376632,5-DifluorobenzaldehydeHCID 517045Sodium Acetate

생성물 1

HCID 67388890trans-6-(2,5-Difluorophenyl)-1-benzyl-5-nitropiperidin-2-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2,5-difluorobenzaldehyde (1.09 g, 7.67 mmol) in ethanol (20 mL) were added methyl 4-nitrobutyrate (1.13 g, 7.04 mmol), benzylamine (0.98 mL, 7.67 mmol), sodium acetate (1.26 g, 15.3 mmol) and acetic acid (0.88 mL, 15.4 mmol). The mixture was stirred at rt for 12 h and then heated at reflux temperature overnight. After evaporation, the residue was purified by column chromatography (silica gel Biotage 40M™) eluting with ethyl acetate/hexane (gradient from 3% to 50%) to give the title compound as the racemic trans isomer. LC-MS: 347.1 (M+1).

후처리

  1. temperatureheated
  2. temperatureat reflux temperature overnight
  3. customAfter evaporation
  4. customthe residue was purified by column chromatography (silica gel Biotage 40M™)
  5. washeluting with ethyl acetate/hexane (gradient from 3% to 50%)

출처 및 근거

ORD 기록
ord-9c81f34126db454a9c58bf2b4af6f2ab
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653059B2

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