Formic Acid → 2-Methyl-2-(1-methyl-piperidin-3(r,s)-yl)-propionic acid methyl ester

HRID 252378ノート

反応式

HRID 252378 の反応式
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]([CH3:13])([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[CH3:6].[CH:15](O)=O.C=O>[OH-].[Na+]>[CH3:2][O:3][C:4](=[O:14])[C:5]([CH3:6])([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH3:15])[CH2:8]1)[CH3:13]

参加物

5

反応物 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 66887928Methyl 2-methyl-2-(piperidin-3-yl)propanoate hydrochloride

生成物 1

HCID 668891612-Methyl-2-(1-methyl-piperidin-3(r,s)-yl)-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

反応条件

温度
60 °C

実験手順

0.370 g of 2-methyl-2-piperidin-3(R,S)-yl-propionic acid methyl ester hydrochloride are dissolved in 0.5 ml of 3M NaOH. 2 ml of formic acid and 0.19 ml of formaldehyde (35% aqueous solution) are added and the reaction solution is warmed to 60° C. for 20 hours. The solution is cooled to room temperature, neutralised with 3M NaOH to pH 8-9 and extracted with dichloromethane (3×10 ml). The combined organic phases are washed with water (10 ml), dried over sodium sulphate and concentrated by evaporation. The residue is purified by means of flash chromatography (SiO2 60F) to provide the title compound as a colourless oil. Rf 0.19 (200:20:1 dichloromethane-methanol-25% conc. ammonia).

後処理

  1. temperatureThe solution is cooled to room temperature
  2. extractionextracted with dichloromethane (3×10 ml)
  3. washThe combined organic phases are washed with water (10 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by means of flash chromatography (SiO2 60F)

出典と根拠

ORDレコード
ord-8dae5724e2f041fd94ccfc3ba6c8e9e6
出典データセット
uspto-grants-2011_01
特許番号
US07868036B2

反応ノート

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