Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate → 4-Piperidinebutanoic acid, ethyl ester

HRID 464880ノート

反応式

HRID 464880 の反応式
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19](Cl)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1

参加物

4

反応物 1

HCID 20143712Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

生成物 1

HCID 106318484-Piperidinebutanoic acid, ethyl ester

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

A solution of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate (10.5 g) in ethanol (20 ml) is catalytically hydrogenated over 10% Palladium-carbon (5 g, 50% wet) as a catalyst at ordinary temperature under atmospheric pressure. After the absorption of hydrogen ceases, the catalyst is removed by filtration and the filtrate is concentrated in vacuo to yield ethyl 4-(4-piperidyl)butyrate, which is dissolved in a mixture of ethyl acetate (200 ml) and water (100 ml). To the solution is added sodium bicarbonate (6 g), and the resulting mixture is stirred at room temperature. Benzyloxycarbonyl chloride (6 ml) is added dropwise to the stirred mixture, and the stirring is continued for 1.5 hours at room temperature. The ethyl acetate layer is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography using hexane:ethyl acetate (3:1) as an eluent to yield ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)butyrate (5.3 g) as a colorless oil.

後処理

  1. customAfter the absorption of hydrogen ceases
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated in vacuo

出典と根拠

ORDレコード
ord-278c2a3e8cd84d748ba314dd07c15edd
出典データセット
uspto-grants-1985_10
特許番号
US04548932

反応ノート

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