(1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】29865

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

【CA登记号】

【分子式】C₁₂H₁₃ClN₂O

【分子量】236.7008

【元素组成】C 60.89% H 5.54% Cl 14.98% N 11.83% O 6.76%

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：(VII)

20) A total synthesis of epibatidine has been reported: The cyclization of 1-(tert-butoxycarbonyl)pyrrole (I) with tosylacetylene (II) by means of H2 over Pd/C in acetonitrile gives the bicyclic compound (III), which is condensed with 5-bromo-2-methoxypyridine (IV) by means of BuLi in THF yielding the 2exo-(6-methoxy-3-pyridyl) derivative (V). The detosylation of (V) by means of Na(Hg) in methanol/THF affords intermediate (VI), which is treated with POCl3 in DMF to effect the conversion of the methoxypyridine into the desired chloropyridine derivative (VII), with simultaneous elimination of the tert-butoxycarbonyl protecting group and N-formylation. Finally, this formyl group is eliminated with HCl in hot THF.

参考文献中间体

合成目标

【1】 Giblin, G.M.P.; Jones, C.D.; Simpkins, N.S.; The total synthesis of the analgesic alkaloid epibatidine. J Chem Soc - Perkins Trans I 1998, 22, 3689.

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)	16432	tert-Butyl pyrrole-1-carboxylate; tert-Butyl-1H-pyrrole-1-carboxylate; tert-Butyl-1-pyrrolecarboxylate	5176-27-2	C₉H₁₃NO₂	详情	详情
(II)	29860	ethynyl 4-methylphenyl sulfone; ethynyl(4-methylphenyl)dioxo-lambda(6)-sulfane	13894-21-8	C₉H₈O₂S	详情	详情
(III)	29861	tert-butyl (1S,4R)-2-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate		C₁₈H₂₃NO₄S	详情	详情
(IV)	29862	5-bromo-2-methoxypyridine; 5-bromo-2-pyridinyl methyl ether	13472-85-0	C₆H₆BrNO	详情	详情
(V)	29863	tert-butyl (1R,2R,3S,4S)-2-(6-methoxy-3-pyridinyl)-3-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]heptane-7-carboxylate		C₂₄H₃₀N₂O₅S	详情	详情
(VI)	29864	tert-butyl (1R,2R,4S)-2-(6-methoxy-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate		C₁₇H₂₄N₂O₃	详情	详情
(VII)	29865	(1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane-7-carbaldehyde		C₁₂H₁₃ClN₂O	详情	详情

Extended Information