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【结 构 式】

【分子编号】29869

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

【CA登记号】

【 分 子 式 】C16H23N3O2

【 分 子 量 】289.37764

【元素组成】C 66.41% H 8.01% N 14.52% O 11.06%

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:(VI)

21) A new synthesis of epibatidine has been reported: The reaction of 2-tosyl-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester (I) with tributyltin hydride (II) by means of azobis(isobutyronitrile) (AIBN) in benzene gives the tin derivative (III), which by treatment with tetrabutylammonium fluoride in THF provides 7-azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester (IV). The condensation of (IV) with 5-iodopyridine-2-amine (V) by means of palladium acetate/tetrabutylammonium chloride/potassium formate in hot DMF yields exo-2-(6-amino-3-pyridyl)-7-azabicyclo[2.2.1]heptane-7-carbo-xylic acid tert-butyl ester (VI), which is finally submitted to diazotization with NaNO2/HCl and treated with CuCl.

1 Abraham, P.; Brieaddy, L.E.; Carroll, F.I.; Lee, J.R.; Liang, F.; New synthesis of 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-2-ene. A key intermediate in the synthesis of epibatidine and analogs. Tetrahedron Lett 1998, 39, 30, 5321.
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) 29861 tert-butyl (1S,4R)-2-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate C18H23NO4S 详情 详情
(II) 29870 butyl(dipentyl)stannane C14H32Sn 详情 详情
(III) 29866 tert-butyl (1R,4S)-2-[butyl(dipentyl)stannyl]-3-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]heptane-7-carboxylate C32H55NO4SSn 详情 详情
(IV) 29867 tert-butyl (1R,4S)-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate C11H17NO2 详情 详情
(V) 29868 5-iodo-2-pyridinamine; 5-iodo-2-pyridinylamine C5H5IN2 详情 详情
(VI) 29869 tert-butyl (1R,2R,4S)-2-(6-amino-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate C16H23N3O2 详情 详情
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