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

HRID 507847노트

반응식

HRID 507847 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매2회

반응 조건

온도
60 °C

실험 절차

0.370 g of 2-methyl-2-piperidin-3(R,S)-yl-propionic acid methyl ester hydrochloride (Example 102) 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 dichlormethane-methanol-25% conc. ammonia).

후처리

  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)

출처 및 근거

ORD 기록
ord-cf09846df8ce4b3886e2a2bc19ddb654
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786307B2

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