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【结 构 式】

【分子编号】16394

【品名】N-[(3R,4S)-4-hydroxy-3-(6-methoxy-3-pyridinyl)cyclohexyl]-4-methylbenzenesulfonamide

【CA登记号】

【 分 子 式 】C19H24N2O4S

【 分 子 量 】376.47664

【元素组成】C 60.62% H 6.43% N 7.44% O 17% S 8.52%

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:rac-(XXVII)

7) Sestanj and his coworkers succeeded in synthesizing epibatidine by a conjugate addition intramolecular displacement strategy.Conjugate addition of higher order cyanocuprate (XXIV) to alpha,beta-unsaturated ketone (XXV) obtained the ketone (XXVI), which was converted to (XXVII) in 60% overall yield. Under Mitsunobu conditions with DEAD and PPh3 as reagents, only the beta-amino-tosylate cyclized to give the epibatidine ring system.

1 Sestanj, K.; Melenski, E.; Jirkovsky, I.; Synthesis of epibatidine. Tetrahedron Lett 1994, 35, 5417-20.
2 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(rac-I) 16385 (+)-Epibatidine hydrochloride; (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane 140111-52-0 C11H13ClN2 详情 详情
(rac-XVIII) 16385 (+)-Epibatidine hydrochloride; (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane 140111-52-0 C11H13ClN2 详情 详情
rac-(XXVI) 16393 (3S,4S)-3-(6-methoxy-3-pyridinyl)-4-[(trimethylsilyl)methyl]cyclohexanone C16H25NO2Si 详情 详情
rac-(XXVII) 16394 N-[(3R,4S)-4-hydroxy-3-(6-methoxy-3-pyridinyl)cyclohexyl]-4-methylbenzenesulfonamide C19H24N2O4S 详情 详情
rac-(XXVIII) 16395 (1R,2R,4S)-2-(6-methoxy-3-pyridinyl)-7-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]heptane; methyl 5-[(1R,2R,4S)-7-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-yl]-2-pyridinyl ether C19H22N2O3S 详情 详情
(XXIV) 16391 (6-Methoxypyridin-3-yl)(2-thienyl)copper dilithium cyanide complex C10H9CuNOS 详情 详情
(XXV) 16392 4-[(trimethylsilyl)methyl]-2-cyclohexen-1-one C10H18OSi 详情 详情
Extended Information