2-chloro-5-[(1S,4R,5S)-2,3-dioxabicyclo[2.2.2]oct-5-yl]pyridine -Drug Synthesis Database

【结构式】

【分子编号】16397

【品名】2-chloro-5-[(1S,4R,5S)-2,3-dioxabicyclo[2.2.2]oct-5-yl]pyridine

【CA登记号】

【分子式】C₁₁H₁₂ClNO₂

【分子量】225.67452

【元素组成】C 58.54% H 5.36% Cl 15.71% N 6.21% O 14.18%

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-(XXX)

8) Ko and his coworkers employed the [4+2] addition reaction of 1-(2-chloro-5-pyridyl)cyclohexa-2,4-diene (XXIX) with singlet oxygen to form the bicyclic peroxide (XXX) as the key step. (XXX) was converted to azidomesylate (XXXI) in 42% overall yield. Based on Broka's epibatidine synthesis, (±)-(I) was obtained through reduction and intramolecular displacement.

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】 Ko, S.Y.; Lerpiniere, J.; Linney, I.D.; Wrigglesworth, R.; The total synthesis of epibatidine. J Chem Soc Ser Chem Commun 1994, 1775-6.

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-(XXX)	16397	2-chloro-5-[(1S,4R,5S)-2,3-dioxabicyclo[2.2.2]oct-5-yl]pyridine		C₁₁H₁₂ClNO₂	详情	详情
rac-(XXXI)	16398	5-((2S,5S)-5-azido-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclohexyl)-2-chloropyridine; (1S,4S)-3-(6-chloro-3-pyridinyl)-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclohexyl azide		C₁₄H₁₉ClN₄OS	详情	详情
(XXIX)	16396	2-chloro-5-(2,4-cyclohexadien-1-yl)pyridine		C₁₁H₁₀ClN	详情	详情

Extended Information