【药物名称】Naltrexone hydrochloride, PTI-901, EN-1639A, Vivitrex, Naltrel(Slow Release), Celupan, Antaxone, ReVia(treatment of alcoholism), Nemexin, Nalorex, Trexan
化学结构式(Chemical Structure):
参考文献No.53409
标题:Naltrexone
作者:Casta馿r, J.; Roberts, P.J.
来源:Drugs Fut 1977,2(1),45
合成路线图解说明:

Compound can be prepared in two different ways both starting from 14-hydroxydihydronormorphinone (I): 1) By reaction of (I) with cyclopropylmethyl bromide (C) in DMF at 70 C. 2) Product (I) is ketalized with ethylene glycol (A) by means of p-toluenesulfonic acid giving the cyclic ketal (II), m.p. 311-3 C; this in turn, is treated with cyclopropyl carbonyl chloride (B) in a mixture of methylene chloride and triethylamine yielding the N,O-dicyclopropylcarbonyl derivative (III), mp 219-20 C. Compound (III) is reduced with LiAlH4, in refluxing THF yielding the ethylene ketal of naltrexone (IV), m.p. 221-2 C, which is finally hydrolyzed with aqueous HCl at 100 C.

参考文献No.701066
标题:14-Hydroxydihydronormorphinone derivatives
作者:Blumberg, H.; et al.
来源:US 3332950
合成路线图解说明:

Compound can be prepared in two different ways both starting from 14-hydroxydihydronormorphinone (I): 1) By reaction of (I) with cyclopropylmethyl bromide (C) in DMF at 70 C. 2) Product (I) is ketalized with ethylene glycol (A) by means of p-toluenesulfonic acid giving the cyclic ketal (II), m.p. 311-3 C; this in turn, is treated with cyclopropyl carbonyl chloride (B) in a mixture of methylene chloride and triethylamine yielding the N,O-dicyclopropylcarbonyl derivative (III), mp 219-20 C. Compound (III) is reduced with LiAlH4, in refluxing THF yielding the ethylene ketal of naltrexone (IV), m.p. 221-2 C, which is finally hydrolyzed with aqueous HCl at 100 C.

参考文献No.701067
标题:Verfahren zur Herstellung von N-substituierten 14-Hydroxydidronormorphinen
作者:Blumberg, H.; et al.
来源:CH 493522; DE 1670616; DE 1795707; GB 1119270
合成路线图解说明:

Compound can be prepared in two different ways both starting from 14-hydroxydihydronormorphinone (I): 1) By reaction of (I) with cyclopropylmethyl bromide (C) in DMF at 70 C. 2) Product (I) is ketalized with ethylene glycol (A) by means of p-toluenesulfonic acid giving the cyclic ketal (II), m.p. 311-3 C; this in turn, is treated with cyclopropyl carbonyl chloride (B) in a mixture of methylene chloride and triethylamine yielding the N,O-dicyclopropylcarbonyl derivative (III), mp 219-20 C. Compound (III) is reduced with LiAlH4, in refluxing THF yielding the ethylene ketal of naltrexone (IV), m.p. 221-2 C, which is finally hydrolyzed with aqueous HCl at 100 C.

参考文献No.701068
标题:D閞iv閟 de 14-hydroxydihydronormorphinones
作者:
来源:FR 6358M
合成路线图解说明:

Compound can be prepared in two different ways both starting from 14-hydroxydihydronormorphinone (I): 1) By reaction of (I) with cyclopropylmethyl bromide (C) in DMF at 70 C. 2) Product (I) is ketalized with ethylene glycol (A) by means of p-toluenesulfonic acid giving the cyclic ketal (II), m.p. 311-3 C; this in turn, is treated with cyclopropyl carbonyl chloride (B) in a mixture of methylene chloride and triethylamine yielding the N,O-dicyclopropylcarbonyl derivative (III), mp 219-20 C. Compound (III) is reduced with LiAlH4, in refluxing THF yielding the ethylene ketal of naltrexone (IV), m.p. 221-2 C, which is finally hydrolyzed with aqueous HCl at 100 C.

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