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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
ノート
印刷プレビュー

反応式

HRID 407996 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 86688117(S)-tert-butyl 2-oxo-1-(piperidin-4-yl)pyrrolidin-3-ylcarbamate

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-bc37b8e0b96747018333c52e78bf8c66
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754226B2

反応ノート

読み込み中…

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