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Trifluoroacetic acid → (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine

HRID 1920781
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반응식

HRID 1920781 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 58581220Tert-butyl (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine-1-carboxylate

생성물 1

HCID 58580794(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine-1-carboxylate (0.95 g, 3.24 mmol), which had been obtained in Example 1 (1d), in methylene chloride (9 mL) was added with trifluoroacetic acid (2.40 mL, 32.3 mmol), and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was added with saturated aqueous sodium hydrogen carbonate solution (20 mL) and extracted with methylene chloride (20 mL×3). After that, the organic layers were dried over sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound as a yellow oily substance (0.44 g, yield 71%).

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe residue was added with saturated aqueous sodium hydrogen carbonate solution (20 mL)
  3. extractionextracted with methylene chloride (20 mL×3)
  4. dry with materialAfter that, the organic layers were dried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-ff307bb3accf4caa9cd36146372a7974
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173631B2

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