Acetic Acid → trans-6-(2,5-Difluorophenyl)-5-nitro-1-(2-pyridin-2-ylethyl)piperidin-2-one

HRID 241576

반응식

HRID 241576 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].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28][NH2:29].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:29]([CH2:28][CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=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 25604Methyl 4-nitrobutyrateHCID 759192-PyridineethanamineHCID 1376632,5-DifluorobenzaldehydeHCID 517045Sodium Acetate

생성물 1

HCID 67389622trans-6-(2,5-Difluorophenyl)-5-nitro-1-(2-pyridin-2-ylethyl)piperidin-2-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2,5-difluorobenzaldehyde (2.29 mL, 21.1 mmol) in ethanol (42 mL) was added methyl 4-nitrobutyrate (2.51 mL, 21.1 mmol) and the mixture stirred for 5 min. To the reaction mixture was added 2-pyridin-2-ylethanamine (2.61 mL, 21.1 mmol) and the mixture stirred for 10 min. To the mixture was added sodium acetate (1.73 g, 21.1 mmol) followed by glacial acetic acid (2.42 mL, 42.2 mmol) and the mixture heated at reflux temperature for 48 h. The solvent was removed in vacuo and to the yellow oil was added saturated aqueous sodium hydrogen carbonate (25 mL) and the aqueous phase extracted with ethyl acetate (4×25 mL). The combined organic phases were washed with saturated aqueous brine (1×25 mL), dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo. The yellow oil was purified by column chromatography (silica gel Biotage 40S™) eluting with ethyl acetate/hexane (gradient from 0% to 100%) to give the racemic trans title compound as a yellow gum. LC/MS 362.2 (M+1).

후처리

  1. stirringthe mixture stirred for 10 min
  2. temperaturethe mixture heated
  3. temperatureat reflux temperature for 48 h
  4. customThe solvent was removed in vacuo and to the yellow oil
  5. additionwas added saturated aqueous sodium hydrogen carbonate (25 mL)
  6. extractionthe aqueous phase extracted with ethyl acetate (4×25 mL)
  7. washThe combined organic phases were washed with saturated aqueous brine (1×25 mL)
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed in vacuo
  11. customThe yellow oil was purified by column chromatography (silica gel Biotage 40S™)
  12. washeluting with ethyl acetate/hexane (gradient from 0% to 100%)

출처 및 근거

ORD 기록
ord-4d534f968d3b48e4bf576eecbea863bb
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653059B2

연결된 노트

불러오는 중…