新型镇痛药opiranserin的合成工艺研究

Synthetic Process of a New Type of Analgesic Drug Opiranserin

本研究改进了新型镇痛药opiranserin(VVZ-149)的合成工艺。用价廉易得的四氢-4H-吡喃-4-酮为起始原料,经过Strecker反应后还原得到4-氨甲基-N,N-二甲基四氢-2H-吡喃-4-胺(3),再与丁香酸(6)缩合得到N-[[4-(二甲胺基)-四氢-2H-吡喃-4-基]甲基]-4-羟基-3,5-二甲氧基苯甲酰胺(7),最后与正溴丁烷发生取代反应得到目标化合物VVZ-149。改进后的工艺反应步骤缩短,总收率从36.2%提高到65.6%,反应条件温和,适合工业化生产。

This study improved the synthetic process of the new analgesic drug opiranserin(VVZ-149).Started from tetrahydro-4H-pyran-4-one,4-(aminomethyl)-N,N-dimethyltetrahydro-2H-pyran-4-amine(3)was obtained by Strecker reaction and reduction.Compound 3 underwent the condensation with syringic acid(6)to obtain N-[[4-(dimethylamino)tetrahydro-2H-pyran-4-yl]methyl]-4-hydroxy-3,5-dimethoxybenzamide(7),and finally substitution with 1-bromobutane reached the target compound VVZ-149.The overall reaction steps were shortened,and the yield was increased from 36.2%to 65.6%.