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

HRID 1276419

反応式

HRID 1276419 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-425195973da8489fb56475316d7a98b3
出典データセット
uspto-grants-2000_12
特許番号
US06166009

関連ノート

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