(+)-2-(7-chloro[1,8]naphthyridin-2-yl)-3-[[(1R,2R,6S,8R)-4-isopentyl-2,9,9-trimethyl-3,5-dioxatricyclo[6.1.1.0(2,6)]dec-4-yl]methyl]-1-isoindolinone -Drug Synthesis Database

【结构式】

【分子编号】47686

【品名】(+)-2-(7-chloro[1,8]naphthyridin-2-yl)-3-[[(1R,2R,6S,8R)-4-isopentyl-2,9,9-trimethyl-3,5-dioxatricyclo[6.1.1.0(2,6)]dec-4-yl]methyl]-1-isoindolinone

【CA登记号】

【分子式】C₃₃H₃₈ClN₃O₃

【分子量】560.13584

【元素组成】C 70.76% H 6.84% Cl 6.33% N 7.5% O 8.57%

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)

The optical resolution of racemic pagoclone (VII) can also be performed by reaction with (-)-(1R,2R,3S,5R)-pinanediol (XIV) by means of PPTS in refluxing dichloroethane to give the ketal (XV) as a diastereomeric mixture separated by crystallization. Finally, hydrolysis of the desired diastereomer (XVI) with 12N HCl affords the (+)-enantiomer, pagoclone.

参考文献中间体

合成目标

【1】 Silvestre, J.S.; Castaner, J.; Leeson, P.A.; Sorbera, L.A.; Pagoclone. Drugs Fut 2001, 26, 7, 651.
【2】 Barreau, M.; Cotrel, C.; Dubroeucq, M.-C.; Manfre, F. (Aventis Pharma SA); Method for preparing enantiomers of an isoindolinone deriv.. WO 9313098 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	47678	2-(7-chloro[1,8]naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone		C₂₃H₂₂ClN₃O₂	详情	详情
(XIV)	16644	(-)-Pinanediol; (1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol	20536-52-1	C₁₀H₁₈O₂	详情	详情
(XV)	47685	(rac)-2-(7-chloro[1,8]naphthyridin-2-yl)-3-[[(1R,2R,6S,8R)-4-isopentyl-2,9,9-trimethyl-3,5-dioxatricyclo[6.1.1.0(2,6)]dec-4-yl]methyl]-1-isoindolinone		C₃₃H₃₈ClN₃O₃	详情	详情
(XVI)	47686	(+)-2-(7-chloro[1,8]naphthyridin-2-yl)-3-[[(1R,2R,6S,8R)-4-isopentyl-2,9,9-trimethyl-3,5-dioxatricyclo[6.1.1.0(2,6)]dec-4-yl]methyl]-1-isoindolinone		C₃₃H₃₈ClN₃O₃	详情	详情

Extended Information