(1R)-1-[4-(benzyloxy)phenyl]-2-bromo-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】62589

【品名】(1R)-1-[4-(benzyloxy)phenyl]-2-bromo-1-ethanol

【CA登记号】

【分子式】C₁₅H₁₅BrO₂

【分子量】307.1869

【元素组成】C 58.65% H 4.92% Br 26.01% O 10.42%

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：(II)

The enantioselective reduction of the phenacyl bromide (I) by means of a culture of Rhodotolule rubra in water gives the a(R)-hydroxy enantiomer (II), which is treated with K2CO3 in refluxing ethanol to yield the chiral epoxide (III). The condensation of (III) with 2-(3,4-dimethoxyphenyl)ethylamine (IV) by means of N,O-bis(trimethylsilyl)acetamide (TMSA) in hot DMSO affords the benzylated precursor (V), which is finally deprotected by means of HCl in water to provide the target Denopamine.

参考文献中间体

合成目标

【1】 Goswami, J.; et al.; A conventient stereoselective synthesis of (R)-(-)-denopamine and (R)-(-)-salmeterol. Tetrahedron Asymmetry 2001, 12, 24, 3343.

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)	36424	1-[4-(benzyloxy)phenyl]-2-bromo-1-ethanone		C₁₅H₁₃BrO₂	详情	详情
(II)	62589	(1R)-1-[4-(benzyloxy)phenyl]-2-bromo-1-ethanol		C₁₅H₁₅BrO₂	详情	详情
(III)	62590	(2R)-2-[4-(benzyloxy)phenyl]oxirane; benzyl 4-[(2R)oxiranyl]phenyl ether		C₁₅H₁₄O₂	详情	详情
(IV)	10098	2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine	120-20-7	C₁₀H₁₅NO₂	详情	详情
(V)	31687	(1R)-1-[4-(benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanol		C₂₅H₂₉NO₄	详情	详情

Extended Information