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【结 构 式】

【分子编号】54245

【品名】(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

【CA登记号】n/a

【 分 子 式 】C19H28O2

【 分 子 量 】288.43012

【元素组成】C 79.12% H 9.78% O 11.09%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

The Birch reduction of 4-butylbenzoic acid (I) with Li in dry ammonia gives 4-butyl-3,4-dihydrobenzoic acid (II), which is submitted to a new Birch reduction to yield 4-butyl-2-cyclohexenecarboxylic acid (III). The methylation of (III) with methanol in acidic medium or with diazomethane, affords the corresponding methyl ester (IV), which is reduced with H2 over PtO2 in ethyl acetate to provide 4-butylcyclohexanecarboxylic acid methyl ester (V). This compound is hydrolyzed with NaOMe in methanol to give the expected carboxylic acid (VI) as a cis/trans mixture. This mixture is dissolved in a minimum amount of methanol, then thiourea and methanol are added and heated until a homogeneous mixture is obtained. The solution is allowed to cool and finally cools at -20 C; the resulting crystalline inclusion complex is filtered and decomposed with aq. KOH to yield trans-4-butylcyclohexanecarboxylic acid (VII) (1). This compound is treated with SOCl2 in benzene to give the corresponding acyl chloride (VIII), which is finally condensed with 14C-labeled testosterone (IX) by means of pyridine in benzene to provide the target labeled testosterone ester.

1 Acosta, C.K.; et al.; Tritium labeled trans-4-N-butyl-2,3-3H-cyclohexanecarboxylic acid. Preparation of testosterone 17beta-trans-4-N-butyl-2,3-3H-cyclohexanecarboxylate and [4-14C]-testosterone 17beta-trans-4-N-butylcyclohexane carboxylate. J Label Compd Radiopharm 1990, 28, 10, 1201.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 54202 4-Butylbenzoic acid; 4-n-Butylbenzoic acid 20651-71-2 C11H14O2 详情 详情
(II) 54203 4-butyl-1,5-cyclohexadiene-1-carboxylic acid n/a C11H16O2 详情 详情
(III) 54204 4-butyl-2-cyclohexene-1-carboxylic acid n/a C11H18O2 详情 详情
(IV) 54025 1,4-Benzenedicarboxylic acid; Benzene-1,4-dicarboxylic acid; p-Benzenedicarboxylic acid; p-Phthalic acid; Terephthalic acid 100-21-0 C8H6O4 详情 详情
(V) 54206 methyl 4-butylcyclohexanecarboxylate n/a C12H22O2 详情 详情
(VI) 54207 4-butylcyclohexanecarboxylic acid n/a C11H20O2 详情 详情
(VII) 54208 trans-4-n-Butylcyclohexanecarboxylic acid 38289-28-0 C11H20O2 详情 详情
(VIII) 54209 4-butylcyclohexanecarbonyl chloride n/a C11H19ClO 详情 详情
(IX) 54210 17beta-Hydroxyandrost-4-en-3-one; 4-Androsten-17-beta-ol-3-one; Android; Androlin; delta4-Androsten-17beta-ol-3-one; Halotensin; Oreton; Testex; Testoderm; Testosterone; Testred; Virilon 58-22-0 C19H28O2 详情 详情
(IX) 54245 (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one n/a C19H28O2 详情 详情
Extended Information