(3aS,7aR)-2-methyltetrahydro-1H-isoindole-1,3,5(2H,4H)-trione 5-(N-phenylhydrazone) -Drug Synthesis Database

【结构式】

【分子编号】31526

【品名】(3aS,7aR)-2-methyltetrahydro-1H-isoindole-1,3,5(2H,4H)-trione 5-(N-phenylhydrazone)

【CA登记号】

【分子式】C₁₅H₁₇N₃O₂

【分子量】271.319

【元素组成】C 66.4% H 6.32% N 15.49% O 11.79%

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：(III)

The condensation of phenyl hydrazine (I) with the cis N-methyl-perhydroisoindoletrione (II) gave hydrazone (III), which underwent Fischer indole synthesis upon treatment with methanolic H2SO4 to afford the pyrrolocarbazole (IV) as the major regioisomer (1). Reduction of the imide group of (IV) with aluminum hydride, generated from LiAlH4 and H2SO4, provided the corresponding amine as a racemic mixture. Separation of the desired (R,R)-enantiomer was then achieved by chiral HPLC on Chiralcel(R) OJ.

参考文献中间体

合成目标

【1】 Berman, B.; Kaufman, J.; Can J Chem 1982, 60, 4, 419-424.
【2】 Pitis, P.M.; Carmosin, R.J.; Carson, J.R. (Ortho-McNeil Pharmaceutical, Inc.); Octahydropyrrolo-[3,4-c]carbazoles useful as analgesic agents. US 6063803; WO 9965911 .

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)	11818	Phenyl hydrazine; 1-Phenylhydrazine	100-63-0	C₆H₈N₂	详情	详情
(II)	31525	(3aS,7aR)-2-methyltetrahydro-1H-isoindole-1,3,5(2H,4H)-trione		C₉H₁₁NO₃	详情	详情
(III)	31526	(3aS,7aR)-2-methyltetrahydro-1H-isoindole-1,3,5(2H,4H)-trione 5-(N-phenylhydrazone)		C₁₅H₁₇N₃O₂	详情	详情
(IV)	31527	(3aR,10cR)-2-methyl-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione		C₁₅H₁₄N₂O₂	详情	详情

Extended Information