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【结 构 式】

【分子编号】10860

【品名】1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl (2R)-4-cyano-2-ethyl-2-(4-pyridinyl)butanoate

【CA登记号】

【 分 子 式 】C34H51N3O4S

【 分 子 量 】597.86276

【元素组成】C 68.31% H 8.6% N 7.03% O 10.7% S 5.36%

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:(XVI-S)

4) The (R)- and (S)-enantiomers of title product are obtained as follows: the trans-esterification of 2-(4-pyridyl)acetic acid methyl ester (XII) with the chiral alcohol (Oppolzer's camphor) (XIII) by means of butyllithium in THF gives the corresponding ester (XIV), which is alkylated with ethyl iodide and potassium hydride in THF yielding a mixture of the corresponding alkylated esters (XVR) and (XVS). The condensation of this mixture with acrylonitrile (IV) by means of potassium tert-butoxide in tert-butanol affords a mixture of the two diastereomeric nitriles (XVIR) and (XVIS), which are easily separable by column chromatography in silica gel. Both isolated compounds are then cyclized with sulfuric acid in refluxing acetic acid.

1 Webster, G.; Thickitt, C.P.; Rowlands, M.G.; Neidle, S.; Jarman, M.; Clissold, D.W.; McCague, R.; Mann, J.; Synthesis of the aromatase inhibitor 3-ethyl-3-(4-pyridyl)piperidine-2,6-dione and its enantiomers. J Chem Soc - Perkins Trans I 1989, 196.
2 Prous, J.; Castaner, J.; Rogletimide. Drugs Fut 1992, 17, 9, 791.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XV-S) 10858 1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl (2S)-2-(4-pyridinyl)butanoate C31H48N2O4S 详情 详情
(XV-R) 10859 1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl (2R)-2-(4-pyridinyl)butanoate C31H48N2O4S 详情 详情
(XVI-S) 10860 1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl (2R)-4-cyano-2-ethyl-2-(4-pyridinyl)butanoate C34H51N3O4S 详情 详情
(XVI-R) 10861 1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl (2R)-4-cyano-2-ethyl-2-(4-pyridinyl)butanoate C34H51N3O4S 详情 详情
(IV) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(XII) 10855 methyl 2-(4-pyridinyl)acetate C8H9NO2 详情 详情
(XIII) 10856 N,N-Dicyclohexyl(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide; (-)-10-Dicyclohexylsulfamoyl-d-isoborneol C22H39NO3S 详情 详情
(XIV) 10857 1-[[(dicyclohexylamino)sulfonyl]methyl]-7,7-dimethylbicyclo[2.2.1]hept-2-yl 2-(4-pyridinyl)acetate C29H44N2O4S 详情 详情
Extended Information