1-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】37969

【品名】1-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-ethanol

【CA登记号】

【分子式】C₁₄H₂₀O₃

【分子量】236.311

【元素组成】C 71.16% H 8.53% O 20.31%

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：(IV)

The alkylation of isovanillin (I) with cyclopentyl bromide (II) and K2CO3 in DMF gives 3-(cyclopentyloxy)-4-methoxybenzaldehyde (III), which is methylated with MeLi in THF yielding the 1-phenylethanol (IV). The oxidation of (IV) with pyridinium dichromate (PDC) in dichloromethane affords the corresponding acetophenone (V), which is treated with NH2OH in pyridine to afford the oxime (VI). Finally, this oxime is treated with NaOCN and TFA in dichloromethane, or with chlorosulfonyl isocyanate in THF.

参考文献中间体

合成目标

【1】 Lombardo, L.J. (American Home Products Corp.); Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents. EP 0470805; GB 2246777; JP 1992253945; US 5124455 .

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)	18455	3-hydroxy-4-methoxybenzaldehyde; Isovanillin	621-59-0	C₈H₈O₃	详情	详情
(II)	10972	1-Bromocyclopentane; Cyclopentyl bromide	137-43-9	C₅H₉Br	详情	详情
(III)	16510	3-(cyclopentyloxy)-4-methoxybenzaldehyde		C₁₃H₁₆O₃	详情	详情
(IV)	37969	1-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-ethanol		C₁₄H₂₀O₃	详情	详情
(V)	37970	1-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-ethanone		C₁₄H₁₈O₃	详情	详情
(VI)	37971	1-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-ethanone oxime		C₁₄H₁₉NO₃	详情	详情

Extended Information