[6-[(2-fluorobenzyl)oxy]-2-naphthyl]methanol -Drug Synthesis Database

【结构式】

【分子编号】51724

【品名】[6-[(2-fluorobenzyl)oxy]-2-naphthyl]methanol

【CA登记号】

【分子式】C₁₈H₁₅FO₂

【分子量】282.3143032

【元素组成】C 76.58% H 5.36% F 6.73% O 11.33%

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：(X)

Reaction of aldehyde (III) with 2-fluorobenzyl alcohol (VIII) by means of triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF furnishes 6-(2-fluorobenzyloxy)naphthalene-2-carbaldehyde (IX) , which is then reduced with NaBH4 in ethanol/THF to give the naphthalenemethanol derivative (X). Halogenation of (X) by means of iodide, triphenylphosphine and imidazole in THF yields the naphthylmethyl iodide derivative (XI), which is finally condensed with thiazolidine-2,4-dione (IV) by means of HMPA and butyl lithium in THF.

参考文献中间体

合成目标

【1】 del Fresno, M.; Sorbera, L.A.; Castaner, J.; Silvestre, J.S.; Netoglitazone. Drugs Fut 2002, 27, 2, 132.
【2】 Ueno, H.; Oe, T.; Suehiro, I.; Nakamura, F. (Mitsubishi Chemical Corp.); Naphthalene derivs.. EP 0604983; JP 1994247945; US 5594016 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	51718	6-hydroxy-2-naphthaldehyde		C₁₁H₈O₂	详情	详情
(IV)	10883	1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione	2295-31-0	C₃H₃NO₂S	详情	详情
(VIII)	51722	2-Fluorobenzyl alcohol	446-51-5	C₇H₇FO	详情	详情
(IX)	51723	6-[(2-fluorobenzyl)oxy]-2-naphthaldehyde		C₁₈H₁₃FO₂	详情	详情
(X)	51724	[6-[(2-fluorobenzyl)oxy]-2-naphthyl]methanol		C₁₈H₁₅FO₂	详情	详情
(XI)	51725	2-[(2-fluorobenzyl)oxy]-6-(iodomethyl)naphthalene; 2-fluorobenzyl 6-(iodomethyl)-2-naphthyl ether		C₁₈H₁₄FIO	详情	详情

Extended Information