Phosphorus oxychloride → Ecgonine

HRID 1604009ノート

反応式

HRID 1604009 の反応式
CN1C2C(C(O)=O)=CCC1CC2.[CH3:13][N:14]1[C@H:18]2[C@@H:19]([C:31]([O:33]C)=[O:32])[C@@H:20]([O:22]C(C3C=CC=CC=3)=O)[CH2:21][C@@H:15]1[CH2:16][CH2:17]2.P(Cl)(Cl)(Cl)=O>Cl>[CH3:13][N:14]1[C@H:18]2[C@@H:19]([C:31]([OH:33])=[O:32])[C@@H:20]([OH:22])[CH2:21][C@@H:15]1[CH2:16][CH2:17]2

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 101709(1R)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acidHCID 446220Cocaine2 回

生成物 1

HCID 91460Ecgonine

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

In later references Anhydroecgonine and esters thereof have been prepared by hydrolysis of cocaine in aqueous hydrochloric acid followed by dehydration with phosphorus oxychloride (J. Amer. Chem. Soc., 82 (1960), page 4643 and EP-A1-604 355 ). Although both the hydrolysis of cocaine and the dehydration of ecgonine produces high yields, it is a serious drawback to this method that the reaction mixture becomes syrupy during the dehydration step which makes stirring almost impossible. Using SOCl2 as dehydrating agent causes similar problems.

出典と根拠

ORDレコード
ord-0b0afd82917d41c289a2c5d583fb1261
出典データセット
uspto-grants-1999_11
特許番号
US05990312

反応ノート

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