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【结 构 式】

【分子编号】16401

【品名】(4R)-2-bromo-4-[[(2,2-dimethylpropanoyl)oxy]amino]-2-cyclohexen-1-one

【CA登记号】

【 分 子 式 】C11H16BrNO3

【 分 子 量 】290.15698

【元素组成】C 45.53% H 5.56% Br 27.54% N 4.83% O 16.54%

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:(XXXIV)

9) The first asymmetric synthesis of (-)-epibatidine was disclosed by Trost and Cook through a Pd-catalyzed desymmetrization of cis-dibenzoyloxy-2-cyclohexene (XXXII) and a Pd-catalyzed cross-coupling reaction. Dibenzoate (XXXII) was reacted with trimethylsilylazide in the presence of a Pd catalyst with chiral phosphine ligands to give ent-(XXXIII) in excellent yield and e.e. (XXXIII) was converted to vinyl bromide (XXXIV), which was coupled with the stable organostannane (XXXV) through a Pd(0)-catalyzed reaction to give enone (XXXVI). Reduction of the double bond and carbonyl, O-mesylation of the resulting amido alcohol and finally heating of the crude amino mesylate in acetonitrile produced (-)-epibatidine.

1 Trost, B.M.; Cook, G.R.; An asymmetric synthesis of (-)-epibatidine. Tetrahedron Lett 1996, 37, 7485-8.
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 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-(XXXII) 16399 (1S,4R)-4-(benzoyloxy)-2-cyclohexen-1-yl benzoate C20H18O4 详情 详情
(XXXIII) 16400 (1S,4R)-4-azido-2-cyclohexen-1-yl benzoate C13H13N3O2 详情 详情
(XXXIV) 16401 (4R)-2-bromo-4-[[(2,2-dimethylpropanoyl)oxy]amino]-2-cyclohexen-1-one C11H16BrNO3 详情 详情
(XXXV) 16402 2-chloro-5-(tributylstannyl)pyridine C17H30ClNSn 详情 详情
(XXXVI) 16403 (4R)-2-(6-chloro-3-pyridinyl)-4-[[(2,2-dimethylpropanoyl)oxy]amino]-2-cyclohexen-1-one C16H19ClN2O3 详情 详情
Extended Information