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

【结 构 式】

【分子编号】10104

【品名】benzyl (2R)-2-[4-(benzyloxy)phenyl]-2-hydroxyethyl(3,4-dimethoxyphenethyl)carbamate

【CA登记号】

【 分 子 式 】C33H35NO6

【 分 子 量 】541.64404

【元素组成】C 73.18% H 6.51% N 2.59% O 17.72%

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:(V)

A new enantioselective synthesis for denopamine has been reported: The acylation of 1-(4-benzyloxyphenyl)-2-[2-(3,4-dimethoxyphenyl)ethylamino]ethanone (I) with benzyloxycarbonyl chloride (II) by means of NaHCO3 in dichloromethane gives the protected aminoketone (III), which is submitted to an asymmetric reduction with (R)-(+)-2-amino-3-methyl-1,1-diphenyl-1-butanol-borane complex in THF yielding the (R)-(-)-protected alcohol (V). Finally, the debenzylation of (V) by hydrogenolysis with H2 over Pd/C in methanol affords denopamine with 96% optical purity.

1 Takeda, M.; Saito, K.; Kawaguchi, T.; Matsuki, K.; Iwakuma, T.; Asymmetric reduction of aromatic ketones. I. Enantioselective synthesis of denopamine. Chem Pharm Bull 1993, 41, 4, 639.
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) 10100 1-[4-(Benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanone; N-(3,4-Dimethoxyphenylethyl)-4-benzyloxyphenacylamine C25H27NO4 详情 详情
(II) 10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(III) 10102 Benzyl 2-[4-(benzyloxy)phenyl]-2-oxoethyl(3,4-dimethoxyphenethyl)carbamate; Benzyl (4-benzyloxy)phenacyl-(3,4-dimethoxyphenethyl)carbamate C33H33NO6 详情 详情
(IV) 10103 (2R)-2-Amino-3-methyl-1,1-diphenyl-1-butanol 56755-20-5 (hydrochloride) C17H21NO 详情 详情
(V) 10104 benzyl (2R)-2-[4-(benzyloxy)phenyl]-2-hydroxyethyl(3,4-dimethoxyphenethyl)carbamate C33H35NO6 详情 详情
Extended Information