methyl (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】16424

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

【CA登记号】

【分子式】C₁₃H₁₅ClN₂O₂

【分子量】266.72708

【元素组成】C 58.54% H 5.67% Cl 13.29% N 10.5% O 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：rac-(LVII)

14) It is noteworthy that Regan et al. described a very concise synthesis of racemic epibatidine. The key step was a reductive Pd-catalyzed Heck-type coupling of the known starting materials olefin (LVI) and 2-chloro-5-iodopyridine (LVII). The desired exo-isomer (LVIII) was formed stereoselectively.

参考文献中间体

合成目标

【1】 Clayton, S.C.; Regan, A.C.; A total synthesis of (±)-epibatidine. Tetrahedron Lett 1993, 34, 7493-6.
【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	分子式	供应商	用于合成
rac-(LIV)	16420	methyl (1S,4R)-2-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hepta-2,5-diene-7-carboxylate	C₁₅H₁₅NO₄S	详情	详情
rac-(LV)	16421	methyl (1S,4R)-2-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate	C₁₅H₁₇NO₄S	详情	详情
rac-(LVI)	16422	methyl (1R,4S)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate	C₈H₁₁NO₂	详情	详情
rac-(LVII)	16424	methyl (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate	C₁₃H₁₅ClN₂O₂	详情	详情
(LVII)	16423	2-chloro-5-iodopyridine	C₅H₃ClIN	详情	详情

Extended Information