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【结 构 式】

【分子编号】11248

【品名】9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol

【CA登记号】

【 分 子 式 】C12H16N2O

【 分 子 量 】204.27192

【元素组成】C 70.56% H 7.89% N 13.71% O 7.83%

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:(V)

The monohydroxylated metabolite of NIK-247, (+)-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol (VI) has been synthesized as follows: The condensation of cyclohexane-1,3-dione (I) with 2-amino-1-cyclopentene-1-carbonitrile (II) by means of PPE gives 2-(3-oxo-1-cyclohexen-1-yl)-1-cyclopentene-1-carbonitrile (III), which is cyclized by means of BF3.Et2O to yield 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-one (IV). The reduction of (IV) with NaBH4 affords the corresponding racemic alcohol (V), which is submitted to optical resolution with (+)-di-p-toluyltartaric acid to give the desired compound (VI).

1 Inada, H.; Yano, M.; Komatsu, T.; Iwamoto, M.; Suzuki, K.; Okada, K.; Synthesis of estimated metabolites of 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline monohydrochloride monohydrate (NIK-247). I.Synthesis of mono-hydroxylated metabolites. Yakugaku Zasshi 1995, 115, 12, 1016.
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) 11244 1,3-Cyclohexanedione 504-02-9 C6H8O2 详情 详情
(II) 11242 2-Amino-1-cyclopentene-1-carbonitrile C6H8N2 详情 详情
(III) 11246 2-[(3-Oxo-1-cyclohexen-1-yl)amino]-1-cyclopentene-1-carbonitrile C12H14N2O 详情 详情
(IV) 11247 9-Amino-1,2,3,5,6,7-hexahydro-8H-cyclopenta[b]quinolin-8-one C12H14N2O 详情 详情
(V) 11248 9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol C12H16N2O 详情 详情
(VI) 63081 (+)-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol C12H16N2O 详情 详情
Extended Information