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

HRID 1683735ノート

反応式

HRID 1683735 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ffe373932e374bbb8dee875c316b1ec0
出典データセット
uspto-grants-1997_06
特許番号
US05639766

反応ノート

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