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【结 构 式】 
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【分子编号】33612 【品名】 【CA登记号】 |
【 分 子 式 】C26H29NO7 【 分 子 量 】467.5188 【元素组成】C 66.8% H 6.25% N 3% O 23.96% |
合成路线1
该中间体在本合成路线中的序号：(III)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.
| 【1】 Blumberg, H.; et al.; 14-Hydroxydihydronormorphinone derivatives. US 3332950 . |
| 【2】 Blumberg, H.; et al.; Verfahren zur Herstellung von N-substituierten 14-Hydroxydidronormorphinen. CH 493522; DE 1670616; DE 1795707; GB 1119270 . |
| 【3】 Derives de 14-hydroxydihydronormorphinones. FR 6358M . |
| 【4】 Castaner, J.; Roberts, P.J.; Naltrexone. Drugs Fut 1977, 2, 1, 45. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 11295 | Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol | 107-21-1 | C2H6O2 | 详情 | 详情 |
| (B) | 14061 | Cyclopropanecarbonyl chloride; Cyclopropanecarboxylic acid chloride | 4023-34-1 | C4H5ClO | 详情 | 详情 |
| (I) | 33610 | (1S,5R,13R,17R)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one | C16H17NO4 | 详情 | 详情 | |
| (II) | 33611 | C18H21NO5 | 详情 | 详情 | ||
| (III) | 33612 | C26H29NO7 | 详情 | 详情 | ||
| (IV) | 33613 | C22H27NO5 | 详情 | 详情 | ||
| (C) | 22277 | Cyclopropyl bromide; 1-(Bromomethyl)cyclopropane | 7051-34-5 | C4H7Br | 详情 | 详情 |