6-[(2R)oxiranyl]-4H-1,3-benzodioxine -Drug Synthesis Database

【结构式】

【分子编号】62576

【品名】6-[(2R)oxiranyl]-4H-1,3-benzodioxine

【CA登记号】

【分子式】C₁₀H₁₀O₃

【分子量】178.1876

【元素组成】C 67.41% H 5.66% O 26.94%

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 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 6-(4-phenylbutoxy)hexylamine (IV) by means of N,O-bis(trimethylsilyl)acetamide (TMSA) in hot DMSO affords the precursor (V), which is finally deprotected by means of HCl in water to provide the target (R)-salmeterol.

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	分子式	供应商	用于合成
(I)	62574	1-(4H-1,3-benzodioxin-6-yl)-2-bromo-1-ethanone	C₁₀H₉BrO₃	详情	详情
(II)	62575	(1R)-1-(4H-1,3-benzodioxin-6-yl)-2-bromo-1-ethanol	C₁₀H₁₁BrO₃	详情	详情
(III)	62576	6-[(2R)oxiranyl]-4H-1,3-benzodioxine	C₁₀H₁₀O₃	详情	详情
(IV)	62577	6-(4-phenylbutoxy)-1-hexanamine; 6-(4-phenylbutoxy)hexylamine	C₁₆H₂₇NO	详情	详情
(V)	62578	(1R)-1-(4H-1,3-benzodioxin-6-yl)-2-{[6-(4-phenylbutoxy)hexyl]amino}-1-ethanol	C₂₆H₃₇NO₄	详情	详情

Extended Information