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【结 构 式】

【分子编号】16436

【品名】tert-butyl (1R,2S,4S)-2-(6-chloro-3-pyridinyl)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate

【CA登记号】

【 分 子 式 】C16H21ClN2O3

【 分 子 量 】324.80712

【元素组成】C 59.17% H 6.52% Cl 10.92% N 8.62% O 14.78%

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-(IX)

16) A similar approach was described by Zhang and Trudell in a recent report: The known 7-azabicyclo[2.2.1]heptan-2-one (VIII) was conveniently synthesized by the [4+2] cycloaddition of methyl 3-bromopropynoate (LXVII) and N-BOC-pyrrole (LXVI). They modified Fletcher's synthesis rendering it more stereoselective and suitable for the preparation of (I) on a large scale. The tertiary alcohol (IX) was successfully deoxygenated by a radical reaction via its methyl oxalyl ester with Bu3SnH in the presence of AIBN. This afforded the deoxygenated product stereoselectively as the endo-isomer (Xa).

1 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210.
2 Zhang, C.; Trudell, M.L..; A short and efficient total synthesis of (±)-epibatidine. J Org Chem 1996, 61, 20, 7189-91.
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-(LXVIII) 16434 7-(tert-butyl) 2-methyl (1S,4R)-3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate C13H16BrNO4 详情 详情
rac-(VIII) 16435 tert-butyl (1R,4S)-2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate C11H17NO3 详情 详情
rac-(IX) 16436 tert-butyl (1R,2S,4S)-2-(6-chloro-3-pyridinyl)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate C16H21ClN2O3 详情 详情
rac-(Xa) 16437 tert-butyl (1R,2S,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate C16H21ClN2O2 详情 详情
rac-(Xb) 16438 tert-butyl (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate C16H21ClN2O2 详情 详情
(LXVI) 16432 tert-Butyl pyrrole-1-carboxylate; tert-Butyl-1H-pyrrole-1-carboxylate; tert-Butyl-1-pyrrolecarboxylate 5176-27-2 C9H13NO2 详情 详情
(LXVII) 16433 methyl 3-bromo-2-propynoate C4H3BrO2 详情 详情
Extended Information