Trifluoroacetic acid → 1-Benzyl-3-nitro-4-phenylpyrrolidine

HRID 910446노트

반응식

HRID 910446 반응식
CO[CH2:3][N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Si](C)(C)C.[N+:17](/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([O-:19])=[O:18].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:10]([N:4]1[CH2:5][CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]([N+:17]([O-:19])=[O:18])[CH2:3]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5284459beta-nitrostyrene, (E)-

생성물 1

HCID 580091801-Benzyl-3-nitro-4-phenylpyrrolidine수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
25 °C

실험 절차

A solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (0.50 g, 2.02 mmol) in CH2Cl2 (15 ml) was added drop wise, over a 30 minutes period, to a stirred solution of ((E)-2-nitro-vinyl)-benzene (0.30 g, 2.02 mmol) and trifluoroacetic acid (0.17 ml, 0.2 mmol) in CH2Cl2 (10 ml) at 0° C. The ice bath was removed, and the solution was stirred at 25° C. for an additional 48 h. It was then concentrated and purification by flash chromatography (SiO2, EtOAc/H 1:6) afforded 0.38 g (68%) of the title compound as a colorless oil. ES-MS m/e: 283 (M+H+).

후처리

  1. customat 0° C
  2. customThe ice bath was removed
  3. concentrationIt was then concentrated
  4. custompurification by flash chromatography (SiO2, EtOAc/H 1:6)

출처 및 근거

ORD 기록
ord-d49992a8ffa04fe1891d720f8da8f9f2
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022099B2

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