Tert-butyl 4-isothiocyanatopiperidine-1-carboxylate → tert-Butyl 4-(3-((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-yl)thioureido)piperidine-1-carboxylate

HRID 451522노트

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HRID 451522 반응식
[NH2:1][N:2]1[CH2:7][CH:6]([OH:8])[CH2:5][CH:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[Cl:16])[C:3]1=[O:17].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([N:31]=[C:32]=[S:33])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CC(N(C)C)=O.C(OCC)(=O)C>[Cl:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[CH:4]1[CH2:5][CH:6]([OH:8])[CH2:7][N:2]([NH:1][C:32](=[S:33])[NH:31][CH:28]2[CH2:27][CH2:26][N:25]([C:23]([O:22][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:24])[CH2:30][CH2:29]2)[C:3]1=[O:17]

참가 물질

5

반응물 2

HCID 58591952Tert-butyl 4-isothiocyanatopiperidine-1-carboxylateHCID 67344225(3SR,5SR)-1-Amino-3-(2-chloro-4-fluorophenyl)-5-hydroxypiperidin-2-one

생성물 1

HCID 86656717tert-Butyl 4-(3-((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-yl)thioureido)piperidine-1-carboxylate수율 83%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

To a solution of (3SR,5SR)-1-amino-3-(2-chloro-4-fluorophenyl)-5-hydroxypiperidin-2-one (0.8 g, 2.9 mmol) in dimethylacetamide (1 mL) was added 4-isothiocyanatopiperidine-1-carboxylic acid tert-butyl ester (0.8 g, 3.2 mmol, US2006/14958A1) and the reaction stirred for 2 hours at 80° C. The reaction was diluted with ethyl acetate, washed with water, brine, dried with sodium sulfate and the solvent was evaporated in vacuo. The product was triturated from dichloromethane by addition of heptane to afford the title compound as a colourless powder (1.2 g, 83%). MS ISP (m/e): 501.2 [(M+H)+].

후처리

  1. washwashed with water, brine
  2. dry with materialdried with sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe product was triturated from dichloromethane by addition of heptane

출처 및 근거

ORD 기록
ord-7a638818a2e947d88a34a747fd171dd0
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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