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【结 构 式】

【分子编号】38039

【品名】2-[(1S)-1-(hydroxymethyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione

【CA登记号】

【 分 子 式 】C12H11NO3

【 分 子 量 】217.22428

【元素组成】C 66.35% H 5.1% N 6.45% O 22.1%

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 enantiocontrolled addition of phthalimide (I) to 1,3-butadiene monoepoxide (II) with a chiral palladium catalyst and Na2CO3 in dichloromethane gives N-(2-hydroxy-1(S)-vinylethyl)phthalimide (III), which is treated with triflic anhydride and TEA in dichloromethane to yield the triflate (IV). The condensation of (IV) with dimethyl malonate (V) by means of NaH in THF affords the alkylated malonate (VI), which is finally decarboxylated and deprotected by a treatment with aqueous refluxing HCl. Note that the synthesis of the biologically active (S)-enantiomer simply requires a change in the chirality of the Pd catalyst used in the first step of the synthesis.

1 Trost, B.M.; et al.; Dynamic kinetic asymetric transformation of diene monoepoxides: A practical asymmetric synthesis of vinylglycinol, vigabatrin, and ethambutol. J Am Chem Soc 2000, 122, 25, 5968.
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) 12376 Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione 85-41-6 C8H5NO2 详情 详情
(II) 32805 2-vinyloxirane 930-22-3 C4H6O 详情 详情
(III) 38039 2-[(1S)-1-(hydroxymethyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione C12H11NO3 详情 详情
(IV) 38040 (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-butenyl trifluoromethanesulfonate C13H10F3NO5S 详情 详情
(V) 19373 dimethyl malonate;Methyl malonate;Propanedioic acid dimethyl ester 108-59-8 C5H8O4 详情 详情
(VI) 38041 dimethyl 2-[(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-butenyl]malonate C17H17NO6 详情 详情
Extended Information