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【结 构 式】

【分子编号】16376

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

【CA登记号】

【 分 子 式 】C16H21ClN2O2

【 分 子 量 】308.80772

【元素组成】C 62.23% H 6.85% Cl 11.48% N 9.07% O 10.36%

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:(Xa)

2) Fletcher and his group also utilized an intramolecular displacement to construct the azabicycloheptane ring system.4-Benzylamino-1,2-epoxycyclohexane (V) was cyclized in N-methyl-pyrrolidone upon heating to yield the exo-alcohol (VI), which was further converted into ketone (VIII). Introduction of the pyridyl group, dehydration and catalytic hydrogenation resulted primarily in the endo-isomer (Xa), which could be epimerized using t-BuOK to afford the more stable exo-isomer (Xb). Fletcher et al. also succeeded in separating the enantiomers of (VII) as their Mosher ester and in establishing the absolute configuration of (I) as (1R,2R,4S).

1 Fletcher, S.R.; Baker, R.; Chambers, M.S.; Hobbs, S.C.; Mitchell, P.J.; The synthesis of (+)- and (-)-epibatidine. J Chem Soc Ser Chem Commun 1993, 1216-8.
2 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210.
3 Fletcher, S.R.; Baker, R.; Chambers, M.S.; Herbert, R.H.; Hobbs, S.C.; Thomas, S.R.; Verrier, H.M.; Watt, A.P.; Ball, R.G.; Total synthesis and determination of the absolute configuration of epibatidine. J Org Chem 1994, 59, 7, 1771-8.
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-(VI) 16372 (1R,2S,4S)-7-benzyl-7-azabicyclo[2.2.1]heptan-2-ol C13H17NO 详情 详情
(Xa) 16376 (1R,2S,4S)-2-(6-chloro-3-pyridinyl)-7-[(2,2-dimethylpropanoyl)oxy]-7-azabicyclo[2.2.1]heptane C16H21ClN2O2 详情 详情
(Xb) 16377 (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-[(2,2-dimethylpropanoyl)oxy]-7-azabicyclo[2.2.1]heptane C16H21ClN2O2 详情 详情
(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
(V) 16371 N-benzyl-7-oxabicyclo[4.1.0]heptan-3-amine; N-benzyl-N-(7-oxabicyclo[4.1.0]hept-3-yl)amine C13H17NO 详情 详情
(VII) 16373 (1R,2S,4S)-7-[(2,2-dimethylpropanoyl)oxy]-7-azabicyclo[2.2.1]heptan-2-ol C11H19NO3 详情 详情
(VIII) 16374 (1R,4S)-7-[(2,2-dimethylpropanoyl)oxy]-7-azabicyclo[2.2.1]heptan-2-one C11H17NO3 详情 详情
(IX) 16375 (1R,2S,4S)-2-(6-chloro-3-pyridinyl)-7-[(2,2-dimethylpropanoyl)oxy]-7-azabicyclo[2.2.1]heptan-2-ol C16H21ClN2O3 详情 详情
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