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【结 构 式】

【分子编号】58460

【品名】methyl 1-[(methoxycarbonyl)amino]cyclopropanecarboxylate

【CA登记号】

【 分 子 式 】C7H11NO4

【 分 子 量 】173.16868

【元素组成】C 48.55% H 6.4% N 8.09% O 36.96%

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)

Partial hydrolysis of dimethyl 1,1-cyclopropanedicarboxylate (I) yields mono-acid (II). Curtius rearrangement of (II), followed by treatment with methanol provides the methyl carbamate (III), which is N-methylated to (IV) employing iodomethane and NaH in DMF. Reduction of the carboxylate and carbamate groups of (IV) by means of LiAlH4 furnishes amino alcohol (V). After chlorination of (V) with SOCl2, the resultant alkyl chloride (VI) is displaced by NaCN to afford nitrile (VII). Hydrolysis of (VII) with methanolic HCl leads to ester (VIII), which is further reduced to amino alcohol (IX) using LiAlH4. Acylation of alcohol (IX) with dimethylcarbamoyl chloride produces the target amino carbamate, which is finally isolated as the corresponding fumarate salt.

1 Guillonneau, C.; Lestage, P.; Charton, Y.; Lockhart, B.; Goldstein, S. (Servier Laboratoires); 1,1- And 1,2-disubstd. cyclopropanes, process for their preparation and pharmaceutical compsns. thereof. EP 1170281; FR 2810664; JP 2002069046; US 2002022643 .
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) 58458 dimethyl 1,1-cyclopropanedicarboxylate; cyclopropane-1,1-dicarboxylic acid dimethyl ester; 1,1-cyclopropanedicarboxylic acid dimethyl ester 6914-71-2 C7H10O4 详情 详情
(II) 58459 1-(methoxycarbonyl)cyclopropanecarboxylic acid 113020-21-6 C6H8O4 详情 详情
(III) 58460 methyl 1-[(methoxycarbonyl)amino]cyclopropanecarboxylate C7H11NO4 详情 详情
(IV) 58461 methyl 1-[(methoxycarbonyl)(methyl)amino]cyclopropanecarboxylate C8H13NO4 详情 详情
(V) 58462 [1-(dimethylamino)cyclopropyl]methanol C6H13NO 详情 详情
(VI) 58463 1-(chloromethyl)-N,N-dimethylcyclopropanamine; N-[1-(chloromethyl)cyclopropyl]-N,N-dimethylamine C6H12ClN 详情 详情
(VII) 58464 2-[1-(dimethylamino)cyclopropyl]acetonitrile C7H12N2 详情 详情
(VIII) 58465 methyl 2-[1-(dimethylamino)cyclopropyl]acetate C8H15NO2 详情 详情
(IX) 58466 2-[1-(dimethylamino)cyclopropyl]-1-ethanol C7H15NO 详情 详情
Extended Information