消炎镇痛药萘普生不对称合成

ASYMMETRIC SYNTHESIS OF NAPROXEN,AN ANTIINFLAMMATERY ANALGESIC

目的：不对称合成非麻醉性消炎镇痛药萘普生［（Ｓ）（＋）２（６′甲氧基２′萘基）丙酸］。方法：以（２Ｒ，３Ｒ）酒石酸二甲酯为手性辅助剂，６甲氧基２丙酰基萘经缩酮化、不对称溴化、水解、重排和催化氢转移氢解等反应合成了光学活性萘普生。结果：化学总收率５４％。制备的萘普生的光学纯度（［α］２５Ｄ＋６３５°）符合中华人民共和国药典（１９９５年版）的要求。结论：不对称合成萘普生的化学收率和光学收率较高。

AIM: To systhesize naproxen by asymmetric method. METHODS: Naproxen was systhesized by acetalization, asymmetric bromination, hydrolysis, rearrangement and catalytic tranfer hydrogenolysis from 6methoxy2propionyl naphthalene, using (2R,3R)dimethyltartrate as chiral auxiliary, Br2 as brominating agent, KH2PO4 as rearrangement agent, 10% PdC/HCO2NH4 as catalytic transfer hydrogenolytic agent. RESULTS: Total yield was 54%, e.e. value of product was 94%. CONCLUSION: The higher chemical yield and optical yield were obtained.