Ethanol → (S)-Ethyl piperidine-2-carboxylate hydrochloride

HRID 1166431

반응식

HRID 1166431 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].S(Cl)([Cl:12])=O.[CH2:14](O)[CH3:15]>>[ClH:12].[CH2:14]([O:8][C:7]([C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:1]1)=[O:9])[CH3:15]

참가 물질

4

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 439227Pipecolic acid, (-)-

생성물 1

HCID 49802334(S)-Ethyl piperidine-2-carboxylate hydrochloride수율 35%

실험 절차

Crude (S)(−)-2-piperidinecarboxylic acid (19.5 g, prepared as described in example 26) was suspended in ethanol (250 ml), and thionyl chloride (40 ml, 0.46 mol) was added dropwise. After addition was complete, the suspension was heated at reflux temperature for 2 h. The mixture was filtered hot, and the filtrate was cooled to room temperature. Filtration and evaporation in vacuo afforded an oil, which was crystallised by rubbing. Ethanol (10 ml) was added, followed by slow addition of diethyl ether (150 ml). The precipitated solid was filtered off, washed with diethyl ether and dried by suction to give 13.8 g (35% calculated from 2-piperidinecarboxylic acid) (S)-(−)-2-piperidinecarboxylic acid ethyl ester hydrochloride.

후처리

  1. additionAfter addition
  2. temperaturethe suspension was heated
  3. temperatureat reflux temperature for 2 h
  4. filtrationThe mixture was filtered hot
  5. filtrationFiltration and evaporation in vacuo
  6. customafforded an oil, which
  7. customwas crystallised
  8. additionEthanol (10 ml) was added
  9. additionfollowed by slow addition of diethyl ether (150 ml)
  10. filtrationThe precipitated solid was filtered off
  11. washwashed with diethyl ether
  12. customdried by suction

출처 및 근거

ORD 기록
ord-44231bd66d024109850fc4d83baff0b8
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613791B1

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