Potassium Carbonate → (R)-1-(2-(((2-phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

HRID 1683735노트

반응식

HRID 1683735 반응식
[C:1]1([C:7]2[C:8](=[N:13][OH:14])[CH2:9][CH2:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:16]([O:18][C:19]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28]Br)[CH2:22]1)=[O:20])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:16]([O:18][C:19]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28][O:14][N:13]=[C:8]2[CH2:9][CH2:10][CH2:11][CH:12]=[C:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:22]1)=[O:20])[CH3:17]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 604484N-(2-phenylcyclohex-2-en-1-ylidene)hydroxylamineHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

생성물 1

HCID 54444134(R)-1-(2-(((2-phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester수율 37.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of the above oxime (0.55 g, 2.9 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (1.0 g, 2.9 mmol, EP 374801A), potassium carbonate (1.0 g, 7.3 mmol) and acetone (25 ml) was stirred at ambient temperature for 14 days. The mixture was filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel (125 g, heptane/ethyl acetate=1/1) to give 0.4 g of (R)-1-(2-(((2-phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

후처리

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (125 g, heptane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-ffe373932e374bbb8dee875c316b1ec0
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639766

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