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Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → 1-[(3RS,4SR)-1-Benzyl-4-(2,4-difluoro-phenyl)-pyrrolidin-3-yl]-ethanone

HRID 906904
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HRID 906904 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.[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1/[CH:25]=[CH:26]/[C:27](=[O:29])[CH3:28]>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:10]([N:4]1[CH2:3][CH:25]([C:19]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=2[F:17])[CH:26]([C:27](=[O:29])[CH3:28])[CH2:5]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
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참가 물질

5

반응물 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 58310994(E)-4-(2,4-difluorophenyl)but-3-en-2-one

생성물 1

HCID 669992391-[(3RS,4SR)-1-Benzyl-4-(2,4-difluoro-phenyl)-pyrrolidin-3-yl]-ethanone수율 89.8%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid촉매HCID 6344Dichloromethane용매2회

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온도
25 °C

실험 절차

A solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (7.82 g, 32.9 mmol) in CH2Cl2 (40 mL) was added dropwise, over a 30 minutes period, to a stirred solution of (E)-4-(2,4-difluoro-phenyl)-but-3-en-2-one (4.0 g, 21.9 mmol) and trifluoroacetic acid (0.17 mL, 0.21 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, CH2Cl2/MeOH 98:2) afforded 6.2 g (89%) of the title compound as a yellow oil. ES-MS m/e: 316.1 (M+H+).

후처리

  1. customThe ice bath was removed
  2. concentrationIt was then concentrated
  3. custompurification by flash chromatography (SiO2, CH2Cl2/MeOH 98:2)

출처 및 근거

ORD 기록
ord-966b7dfc8c7a4d9b9641ec034bf142d7
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012998B2

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