Diethyl Malonate → Diethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)malonate

HRID 225471

反応式

HRID 225471 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](C2C=CC=CC=2S([O-])(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].[O-]CC.[Na+].CCO>CCO>[CH2:33]([O:32][C:24](=[O:31])[CH:25]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:34]

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 23706232Ethanol sodium ethoxideHCID 866158511-Tert-butoxycarbonylpiperidine-4-ylbenzenesulfonate

生成物 1

HCID 59605280Diethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)malonate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-tert-butoxycarbonylpiperidine-4-ol, triethylamine, benzenesulfonyl chloride and methylene chloride was stirred for two days at room temperature to give 1-tert-butoxycarbonylpiperidine-4-ylbenzenesulfonate. A mixture of the obtained 1-tert-butoxycarbonylpiperidine-4-ylbenzenesulfonate, diethyl malonate, 20% sodium ethoxide-EtOH solution and EtOH was stirred for 22 hours heated to reflux to give diethyl[1-(tert-butoxycarbonyl)piperidine-4-yl]malonate. A mixture of the obtained diethyl[1-(tert-butoxycarbonyl)piperidine-4-yl]malonate, lithium borohydride, toluene and THF was stirred for 18 hours at 60° C. to give 2-(1-tert-butoxycarbonylpiperidine-4-yl)propane-1,3-diol. A mixture of the obtained 2-(1-tert-butoxycarbonylpiperidine-4-yl)propane-1,3-diol, 4M HCl-dioxane solution and MeOH was stirred for one hour at room temperature to give 2-piperidine-4-ylpropane-1,3-diol hydrochloride.

後処理

  1. temperatureheated
  2. temperatureto reflux

出典と根拠

ORDレコード
ord-83d2f5a5043c4c058f48fc3d80f22423
出典データセット
uspto-grants-2009_07
特許番号
US07557112B2

関連ノート

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