• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】49439

【品名】methyl 5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenylcarbamate

【CA登记号】

【 分 子 式 】C14H19NO4

【 分 子 量 】265.3092

【元素组成】C 63.38% H 7.22% N 5.28% O 24.12%

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:(XIX)

Condensation of 4-(2,3-dimethoxyphenyl)-2-oxo-3-butenoic acid (VIII) with methyl carbamate (XV) by means of TsOH in refluxing toluene gives the substituted furanone (XVI), which is hydrogenated with H2 over Pd/C in hot ethanol to yield 4-(2,3-dimethoxyphenyl)-2-(methoxycarbonylamino)butyric acid (XVII). Cyclization of acid (XVII) by means of PPA at 60 C affords tetralone (XVIII), which is reduced with H2 over Pd/C in an autoclave at 80 C to provide N-(5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)carbamic acid methyl ester (XIX). Finally, the carbamoyl group of (XIX) is reduced with LiAlH4 in hot THF to yield N-(5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylamine (V).

1 Castaner, J.; Mealy, N.E.; Bayes, M.; Leeson, P.A.; Nolomirole Hydrochloride. Drugs Fut 2001, 26, 11, 1046.
2 Servadio, V.; Ventura, P.; Amari, G.; Chiesi, P.; Del Canale, M.; De Fanti, R. (Chiesi Farmaceutici SpA); A process for the preparation of 5,6-dihydroxy-2-amino-1,2,3,4-tetrahydronaphthalene derivs.. WO 9529147 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 37381 N-(5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-N-methylamine; 5,6-dimethoxy-N-methyl-1,2,3,4-tetrahydro-2-naphthalenamine C13H19NO2 详情 详情
(VIII) 37376 (E)-4-(2,3-dimethoxyphenyl)-2-oxo-3-butenoic acid C12H12O5 详情 详情
(XV) 40724 methyl carbamate; carbamic acid methyl ester 598-55-0 C2H5NO2 详情 详情
(XVI) 49436 methyl 5-(2,3-dimethoxyphenyl)-2-oxo-2,5-dihydro-3-furanylcarbamate C14H15NO6 详情 详情
(XVII) 49437 4-(2,3-dimethoxyphenyl)-2-[(methoxycarbonyl)amino]butyric acid C14H19NO6 详情 详情
(XVIII) 49438 methyl 5,6-dimethoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalenylcarbamate C14H17NO5 详情 详情
(XIX) 49439 methyl 5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenylcarbamate C14H19NO4 详情 详情
Extended Information