(1R,9R,10R)-17-(cyclobutylcarbonyl)-17-azatetracyclo[7.5.3.0(1,10).0(2,7)]heptadeca-2,4,6-trien-4-yl cyclobutanecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】43743

【品名】(1R,9R,10R)-17-(cyclobutylcarbonyl)-17-azatetracyclo[7.5.3.0(1,10).0(2,7)]heptadeca-2,4,6-trien-4-yl cyclobutanecarboxylate

【CA登记号】

【分子式】C₂₆H₃₃NO₃

【分子量】407.55296

【元素组成】C 76.62% H 8.16% N 3.44% O 11.78%

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：(IV)

The N-dealkylation of levorphanol (I) by means of phenyl chloroformate gave rise to (-)-3-hydroxymorphinan (II). This was then condensed with cyclobutanecarbonyl chloride (III) to afford the diacyl derivative (IV). The reduction of the amide group of (IV), with concomitant ester cleavage, by means of LiAlH4 furnished the desired compound, which was finally isolated as the mandelate salt.

参考文献中间体

合成目标

【1】 Cohen, D.J.; Mello, N.K.; Zong, R.; Gao, P.; Bidlack, J.M.; Negus, S.S.; Bakthavachalam, V.; Neumeyer, J.L.; Synthesis and opioid receptor affinity of morphinan and benzomorphan derivatives: Mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine dependence. J Med Chem 2000, 43, 1, 114.
【2】 Gates, M.D. Jr.; N-Cyclopropylmethyl- and -cyclobutylmethyl-morphinans. US 3285922 .

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)	43741	(1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0(1,10).0(2,7)]heptadeca-2,4,6-trien-4-ol		C₁₇H₂₃NO	详情	详情
(II)	43742	(1R,9R,10R)-17-azatetracyclo[7.5.3.0(1,10).0(2,7)]heptadeca-2,4,6-trien-4-ol		C₁₆H₂₁NO	详情	详情
(III)	18589	cyclobutanecarbonyl chloride	5006-22-4	C₅H₇ClO	详情	详情
(IV)	43743	(1R,9R,10R)-17-(cyclobutylcarbonyl)-17-azatetracyclo[7.5.3.0(1,10).0(2,7)]heptadeca-2,4,6-trien-4-yl cyclobutanecarboxylate		C₂₆H₃₃NO₃	详情	详情

Extended Information