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【结 构 式】

【分子编号】13013

【品名】(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

【CA登记号】

【 分 子 式 】C19H27NO3

【 分 子 量 】317.42832

【元素组成】C 71.89% H 8.57% N 4.41% O 15.12%

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:(IV)

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
Extended Information