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Potassium Cyanide → (3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-[(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidine-1-carboxylic acid 3-cyano-propyl ester

HRID 910469
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인쇄 미리보기

반응식

HRID 910469 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([F:26])[CH:17]=2)[CH3:14])[CH:10]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:9]1)=[O:7].[C-:35]#[N:36].[K+]>CN(C=O)C>[C:35]([CH2:2][CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[C:18]([F:26])[CH:17]=2)[CH3:14])[CH:10]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:9]1)=[O:7])#[N:36]
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참가 물질

4

반응물 2

HCID 9032Potassium CyanideHCID 72253477(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-[(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidine-1-carboxylic acid 3-chloro-propyl ester

생성물 1

HCID 72253459(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-[(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidine-1-carboxylic acid 3-cyano-propyl ester수율 49.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

To a stirred solution of (3SR,4RS)-3-(3,4-dichloro-phenyl)-4-[(3-fluoro-4-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidine-1-carboxylic acid 3-chloro-propyl ester (XVI-1) (40 mg, 0.068 mmol) in DMF (2 ml) was added potassium cyanide (5.0 mg, 0.077 mmol) and 18 crown 6-ether (18 mg, 0.068 mmol). The reaction mixture was stirred at 40° C. overnight, concentrated under vacuo. The product was purified by preparation HPLC to yield 18 mg (45%) of the title product as a colorless oil. ES-MS m/e: 532.1 (M+H+).

후처리

  1. concentrationconcentrated under vacuo
  2. customThe product was purified by preparation HPLC

출처 및 근거

ORD 기록
ord-2d9adb0e688341109f785ac5d3deba08
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022099B2

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