Trifluoroacetic acid → Ethyl trans-1-benzyl-4-(2,2,2-trifluoroethyl)pyrrolidine-3-carboxylate

HRID 577718노트

반응식

HRID 577718 반응식
[F:1][C:2]([F:12])([F:11])[CH2:3]/[CH:4]=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(O)(C(F)(F)F)=O.[CH2:20]([N:27]([CH2:33]O)[CH2:28][Si](C)(C)C)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH2:20]([N:27]1[CH2:33][C@@H:4]([CH2:3][C:2]([F:11])([F:12])[F:1])[C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 15104041Ethyl 5,5,5-trifluoropent-2-enoate2회HCID 70869782HCID 70869782, 화합물

생성물 1

HCID 57556218Ethyl trans-1-benzyl-4-(2,2,2-trifluoroethyl)pyrrolidine-3-carboxylate수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of ethyl (2E)-5,5,5-trifluoropent-2-enoate (3.0 g, 16.5 mmol) and TFA (0.38 g, 3.3 mmol) in DCM (40 mL) was added dropwise {benzyl[(trimethylsilyl)methyl]amino}methanol (7.8 g, 33 mmol) at 0° C. over a period of 30 min. After the addition, the mixture was refluxed overnight. TLC (petroleum ether:EtOAc 10:1) indicated ethyl (2E)-5,5,5-trifluoropent-2-enoate was consumed. The reaction mixture was washed with sat. NaHCO3 (40 mL), brine (40 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether:EtOAc=100:1 to 10:1) to give the title compound (5.1 g, 98% yield) as a yellow oil.

후처리

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed overnight
  3. customwas consumed
  4. washThe reaction mixture was washed with sat. NaHCO3 (40 mL), brine (40 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether:EtOAc=100:1 to 10:1)

출처 및 근거

ORD 기록
ord-32089947bf5240b89045271dcf6c6daf
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040547B2

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