Process for preparing &bgr;-hydroxycarbamates and their conversion to oxazolidinones
申请人:Merck & Co., Inc.
公开号:US06372911B1
公开(公告)日:2002-04-16
A process for preparing a &bgr;-hydroxy carbamate product is disclosed. The process comprises reacting an olefin compound containing at least one carbon-carbon double bond with a carbamate in an aqueous solvent and in the presence of a base, an osmium catalyst, a co-oxidant selected from a halohydantoin, a haloisocyanuric acid, and an alkali metal salt of a haloisocyanuric acid, and optionally an asymmetric ligand, to form a reaction mixture containing the &bgr;-hydroxy carbamate product. The process optionally further comprises treating the &bgr;-hydroxy carbamate product with additional base to form an oxazolidinone. The oxazolidinones are useful as chiral auxiliary agents and as intermediates for the formation of pharmaceutically active substances such as alpha 1 a adrenergic receptor antagonists. A process for preparing nitrogen-functionalized derivatives of the oxazolidinones is also disclosed.
公开了一种制备β-羟基氨基甲酸酯产物的方法。该方法包括在水溶剂和碱的存在下,将至少含有一个碳-碳双键的烯烃化合物与氨基甲酸酯反应,同时加入铂催化剂、协同氧化剂(选择自卤代二嗪、卤代异氰尿酸和卤代异氰尿酸的碱金属盐)以及可选的不对称配体,形成含有β-羟基氨基甲酸酯产物的反应混合物。该方法还可选地进一步包括使用额外的碱处理β-羟基氨基甲酸酯产物,形成噁唑烷酮。噁唑烷酮可用作手性辅助剂和药物活性物质的中间体,例如α1a肾上腺素受体拮抗剂。还公开了一种制备噁唑烷酮的氮功能化衍生物的方法。