(1R,5S)-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octan-3-one -Drug Synthesis Database

【结构式】

【分子编号】36341

【品名】(1R,5S)-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octan-3-one

【CA登记号】

【分子式】C₁₀H₁₇NO₂

【分子量】183.25052

【元素组成】C 65.54% H 9.35% N 7.64% O 17.46%

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：(XVIII)

Condensation between 2,5-dimethoxytetrahydrofuran (XIV), acetone-1,3-dicarboxylic acid (XV) and 3-amino-1-propanol (XVI), followed by acid decarboxylation of the intermediate adduct (XVII) furnished the tropinone analogue (XVIII). After conversion of (XVIII) to the corresponding oxime (XIX), its hydrogenation over PtO2 gave amine (XX). This was finally coupled with acid chloride (VIII) to give the title amide.

参考文献中间体

合成目标

【1】 Yokomori, S.; Muramatsu, M.; Suzuki, M.; Ito, C.; Asanuma, H.; Isobe, Y.; Ohuchi, Y.; Kaneko, T.; Synthesis and evaluation of novel 2-oxo-1,2-dihydro-3-quinolinecarboxamide derivatives as potent and selective serotonin 5-HT4 receptor agonists. Chem Pharm Bull 2001, 49, 1, 29.
【2】 Ohuchi, Y.; Suzuki, M.; Asanuma, H.; Yokomori, S.; Hatayama, K. (Taisho Pharmaceutical Co., Ltd.); Quinolinecarboxylic acid deriv.. EP 0710662; JP 1996034784; US 5753673; WO 9531455 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	36336	1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarbonyl chloride		C₁₃H₁₂ClNO₂	详情	详情
(XIV)	12132	2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether	696-59-3	C₆H₁₂O₃	详情	详情
(XV)	15530	1,3-Acetonedicarboxylic Acid; 3-Oxopentanedioic acid；3-oxoglutaric acid	542-05-2	C₅H₆O₅	详情	详情
(XVI)	18522	3-amino-1-propanol	156-87-6	C₃H₉NO	详情	详情
(XVII)	36340	(1R,5S)-8-(3-hydroxypropyl)-3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylic acid		C₁₂H₁₇NO₆	详情	详情
(XVIII)	36341	(1R,5S)-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octan-3-one		C₁₀H₁₇NO₂	详情	详情
(XIX)	36342	(1R,5S)-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octan-3-one oxime		C₁₀H₁₈N₂O₂	详情	详情
(XX)	36343	3-[(1R,5S)-3-amino-8-azabicyclo[3.2.1]oct-8-yl]-1-propanol		C₁₀H₂₀N₂O	详情	详情

Extended Information