Phosphorus oxychloride → Ecgonine

HRID 1604009노트

반응식

HRID 1604009 반응식
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

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 101709(1R)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acidHCID 446220Cocaine2회

생성물 1

HCID 91460Ecgonine

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-0b0afd82917d41c289a2c5d583fb1261
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990312

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