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Diisopropylethylamine → (S)-tert-butyl 1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate

HRID 407996
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HRID 407996 반응식
[O:1]=[C:2]1[C@@H:6]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:5][CH2:4][N:3]1[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(C(C)C)C(C)C)C.Cl[C:31]1[C:36]([Cl:37])=[CH:35][C:34]([C:38]([F:41])([F:40])[F:39])=[CH:33][N:32]=1>CN(C=O)C.CCOC(C)=O>[Cl:37][C:36]1[C:31]([N:18]2[CH2:17][CH2:16][CH:15]([N:3]3[CH2:4][CH2:5][C@H:6]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:2]3=[O:1])[CH2:20][CH2:19]2)=[N:32][CH:33]=[C:34]([C:38]([F:40])([F:39])[F:41])[CH:35]=1
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HCID 81531DiisopropylethylamineHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 86688117(S)-tert-butyl 2-oxo-1-(piperidin-4-yl)pyrrolidin-3-ylcarbamate

생성물 1

HCID 67469801(S)-tert-butyl 1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate수율 61.7%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (S)-tert-butyl 2-oxo-1-(piperidin-4-yl)pyrrolidin-3-ylcarbamate (4.0 g, 14 mmol) in DMF (50 mL) was added N-ethyl-N-isopropylpropan-2-amine (5.5 g, 42 mmol) and 2,3-dichloro-5-(trifluoromethyl)pyridine (9.1 g, 42 mmol) and the reaction was stirred overnight at ambient temperature. The reaction was diluted with EtOAc (about 200 mL) and the organic layer was washed with water (100 mL), and brine (50 mL), dried over MgSO4, and concentrated under vacuum. The crude material was purified on silica using a gradient of DCM to 5% EtOAc/DCM as eluent to give (S)-tert-butyl 1-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate (4.0 g, 61%).

후처리

  1. washthe organic layer was washed with water (100 mL), and brine (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe crude material was purified on silica using a gradient of DCM to 5% EtOAc/DCM as eluent

출처 및 근거

ORD 기록
ord-bc37b8e0b96747018333c52e78bf8c66
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754226B2

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