2,2,2-Trichloroethyl chloroformate → 1-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethanone

HRID 1880215노트

반응식

HRID 1880215 반응식
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:10]([C:21](=[O:23])[CH3:22])[CH2:9]1)C1C=CC=CC=1.ClC(OCC(Cl)(Cl)Cl)=O>CC#N>[Cl:20][C:15]1[CH:14]=[C:13]([CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[C:21](=[O:23])[CH3:22])[CH:18]=[CH:17][C:16]=1[Cl:19]

참가 물질

4

반응물 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 669997301-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanone

생성물 1

HCID 671317481-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethanone수율 63.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 1-[(3SR,4RS)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanone 4.00 g (9.20 mmol) dissolved in CH3CN (50 mL) was added 2.48 mL (18.40 mmol) of 2,2,2-trichloroethyl chloroformate and stirring was continued for 3 hours at RT. Volatiles were removed under vacuo, and the residue was dissolved in AcOH (30 mL) before a total of 1.5 g of Zn dust was added portion wise. After three hours at RT, the reaction mixture was filtered on celite, the solvent removed under vacuo, followed by extraction with EtOAc/aq. NaHCO3 (basic pH). The organic phases were dried on Na2SO4 and column chromatography (SiO2, CH2Cl2/MeOH 9:1 to 8:2) yielded the title compound (1.50 g, 63%) as a colorless oil. ES-MS m/e: 258.0 (M+H+).

후처리

  1. customVolatiles were removed under vacuo
  2. dissolutionthe residue was dissolved in AcOH (30 mL) before a total of 1.5 g of Zn dust
  3. additionwas added portion wise
  4. waitAfter three hours at RT
  5. filtrationthe reaction mixture was filtered on celite
  6. customthe solvent removed under vacuo
  7. extractionfollowed by extraction with EtOAc/aq
  8. dry with materialThe organic phases were dried on Na2SO4 and column chromatography (SiO2, CH2Cl2/MeOH 9:1 to 8:2)

출처 및 근거

ORD 기록
ord-59fa68259bb14de5a19b2b57236bee12
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318759B2

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