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【结 构 式】

【分子编号】16454

【品名】[(1R,2R,3R,4S)-7-benzyl-3-(2-oxoethyl)-7-azabicyclo[2.2.1]hept-2-yl]methyl formate

【CA登记号】

【 分 子 式 】C17H21NO3

【 分 子 量 】287.35868

【元素组成】C 71.06% H 7.37% N 4.87% O 16.7%

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:(LXIV)

19) Intramolecular cyclization of substituted proline derivatives. Rapoport et al. developed an asymmetric methodology which had potential for the enantiospecific synthesis of (+)- and (-)-epibatidine. The triflate (LXXIX) was readily synthesized from levulinic acid in 3 straightforward steps. Alkylation of S-thiolactam (LXXX) prepared from L-glutamic acid with triflate (LXXIX), followed by sulfide contraction provided the carbamate (LXXXI). (LXXXI) was then converted into keto acid (LXXXII). (LXXXII) was decarboxylated and the resulting iminium ions were subjected to intramolecular cyclization to give a mixture of trans-2,3-disubstituted-7-azabicyclo[2.2.1]heptanes (LXXXIII) and (LXXXIV). This mixture was selectively converted into (+)- and (-)-N-BOC-7-azabicyclo[2.2.1]heptane-2-ones (VIII), which are versatile intermediates for the enantiospecific synthesis of (+)- and (-)-epibatidine.

1 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210.
2 Hernández, A.; Marcos, M.; Rapoport, H.; Synthesis of (+)- and (-)-N-BOC-7-azabicyclo[2.2.1]heptan-2-ones, versatile intermediates for the enantiospecific synthesis of (+)- and (-)-epibatidine and analogues. J Org Chem 1995, 60, 2638-91.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
((-)-VIII) 16435 tert-butyl (1R,4S)-2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate C11H17NO3 详情 详情
(LXIV) 16454 [(1R,2R,3R,4S)-7-benzyl-3-(2-oxoethyl)-7-azabicyclo[2.2.1]hept-2-yl]methyl formate C17H21NO3 详情 详情
(LXXIX) 16449 methyl 3-(2-methyl-1,3-dioxolan-2-yl)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate C9H13F3O7S 详情 详情
(LXXX) 16450 2-[(2S)-1-benzyl-5-thioxotetrahydro-1H-pyrrol-2-yl]-1,1-dimethylethyl formate C16H21NO2S 详情 详情
(LXXXI) 16451 methyl 2-[(5S)-1-benzyl-5-[2-(formyloxy)-2-methylpropyl]tetrahydro-2H-pyrrol-2-ylidene]-3-(2-methyl-1,3-dioxolan-2-yl)propanoate C24H33NO6 详情 详情
(LXXXII) 16452 methyl (2S)-2-[(2R,5R)-1-benzyl-5-(formyloxy)tetrahydro-1H-pyrrol-2-yl]-4-oxopentanoate C18H23NO5 详情 详情
(LXXXIII) 16453 [(1R,2S,3S,4S)-7-benzyl-3-(2-oxoethyl)-7-azabicyclo[2.2.1]hept-2-yl]methyl formate C17H21NO3 详情 详情
Extended Information