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【结 构 式】 
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【分子编号】13012 【品名】(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid 【CA登记号】 |
【 分 子 式 】C19H29NO3 【 分 子 量 】319.4442 【元素组成】C 71.44% H 9.15% N 4.38% O 15.03% |
合成路线1
该中间体在本合成路线中的序号：(III)Synthesis of 5,6,6-trideuterated finasteride: The reaction of 3-oxo-4-aza-5-androstene-17beta-carboxylic acid (I) with D2O and CH3CO2D gives the monodeuterated compound (II), which, without isolation is hydrogenated with D2 over PtO2 to yield 5,6,6-(D)3-3-oxo-4-aza-5alpha-androstane-17beta-carboxylic acid (III). The dehydrogenation of (III) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and bis(trimethylsilyl)trifluoroacetamide (BSTFA) affords 5,6,6-(D)3-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxylic acid (IV), which is esterified with 2,2'-dithiopyridine (V) and triphenylphosphine in toluene to give the corresponding thioester (VI). Finally, this compound is treated with tert-butylamine (VII) in THF).
| 【1】 Dini, S.; Danza, G.; Guarna, A.; Marrucci, A.; Bartolucci, G.; Serio, M.; Synthesis of 5,6,6-[H-2(3)]finasteride and quantitative determination of finasteride in human plasma at picogram level by an isotope-dilution mass spectrometric method. J Chromatogr B - Biomed Appl 1995, 674, 2, 197. |
| 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) | 13010 | (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-Dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid | C19H27NO3 | 详情 | 详情 | |
| (II) | 13011 | (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-Dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid | C19H27NO3 | 详情 | 详情 | |
| (III) | 13012 | (4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid | C19H29NO3 | 详情 | 详情 | |
| (IV) | 13013 | (4aS,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid | C19H27NO3 | 详情 | 详情 | |
| (V) | 13014 | 3-(3-Pyridinyldisulfanyl)pyridine; Di(3-pyridinyl) disulfide | C10H8N2S2 | 详情 | 详情 | |
| (VI) | 13015 | S-(3-pyridinyl) (4aS,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carbothioate | C24H30N2O2S | 详情 | 详情 |