1-[(1R,2S,4S)-2-hydroxy-2-(3-pyridinyl)-7-azabicyclo[2.2.1]hept-7-yl]-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】16388

【品名】1-[(1R,2S,4S)-2-hydroxy-2-(3-pyridinyl)-7-azabicyclo[2.2.1]hept-7-yl]-1-ethanone

【CA登记号】

【分子式】C₁₃H₁₆N₂O₂

【分子量】232.28232

【元素组成】C 67.22% H 6.94% N 12.06% O 13.78%

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：(XXI)

6) Nakai et al. used 3-lithio pyridine as a nucleophile to attack ketone (XX), yielding the tertiary alcohol (XXI) stereoselectively. Reductive elimination of the hydroxyl group followed by oxidation and acid hydrolysis gave N-oxide (XXII), which was treated with POCl3 to produce (I) and (XXIII) in low yields.

参考文献中间体

合成目标

【1】 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210.
【2】 Senokuchi, K.; Nakai, H.; Kawamura, M.; et al.; Synthesis and biological evaluation of (±)-epibatidine and the congeners. Synlett 1994, 343-4.

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)	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
(XX)	16387	(1R,4S)-7-acetyl-7-azabicyclo[2.2.1]heptan-2-one		C₈H₁₁NO₂	详情	详情
(XXI)	16388	1-[(1R,2S,4S)-2-hydroxy-2-(3-pyridinyl)-7-azabicyclo[2.2.1]hept-7-yl]-1-ethanone		C₁₃H₁₆N₂O₂	详情	详情
(XXII)	16389	3-[(1R,2R,4S)-7-azabicyclo[2.2.1]hept-2-yl]-1-pyridiniumolate		C₁₁H₁₄N₂O	详情	详情
(XXIII)	16390	(1R,2R,4S)-2-(2-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane		C₁₁H₁₃ClN₂	详情	详情

Extended Information