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Potassium Carbonate → (R)-1-(2-(((2-phenyl-2-penten-1-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

HRID 975251
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HRID 975251 반응식
[C:1]1([C:7](=[CH:11][CH2:12][CH3:13])[CH:8]=[N:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27]Br)[CH2:21]1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][O:10][N:9]=[CH:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:11][CH2:12][CH3:13])[CH2:21]1)=[O:19])[CH3:16]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromideHCID 867504432-Phenyl-2-pentenal oxime

생성물 1

HCID 54416283(R)-1-(2-(((2-phenyl-2-penten-1-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester수율 52.7%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of the above oxime (2.0 g, 11 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (3.94 g, 11 mmol), potassium carbonate (4.73 g, 34 mmol) and acetone (25 ml) was stirred at room temperature for 4 days. The mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The residue was purified by column chromatography on silica gel (75 g, cyclohexane/ethyl acetate 3/1) to give 2.08 g of (R)-1-(2-(((2-phenyl-2-penten-1-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester.

후처리

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated from the filtrate in vacuo
  3. customThe residue was purified by column chromatography on silica gel (75 g, cyclohexane/ethyl acetate 3/1)

출처 및 근거

ORD 기록
ord-9c42a732ca604681bd202081a36a32bc
출처 데이터셋
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05608069

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