Chlorination of Aliphatic Primary Alcohols via Triphosgene–Triethylamine Activation
摘要:
Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.
An efficient one-pot route to synthesize tertiary alcohol compounds using Barbier–Grignard reaction of unactivated alkyl or arylbromides with ester in THF at 65 °C catalyzed by CuO has been developed and systematically investigated. A wide range of substituted tertiary alcohol compounds were obtained in good to high yields. The reaction is highly chemoselective. The mechanism involving the leaving
The imidazoline compound represented by the following formula (I):
and its pharmacologically acceptable salts, and the imidazoline compound represented by the following formula (II):
Compound (I) has highly selective antagonistic action on muscarinic M3 receptor subtypes, and especially airway muscarinic M3 receptor subtypes, and is, therefore, particularly useful as a preventive or therapeutic agent for especially, diseases related to muscarinic M3 receptors in chronic obstructive pulmonary disease and asthma, while compound (II) is useful as a production intermediate for compound (I).
Chlorination of Aliphatic Primary Alcohols via Triphosgene–Triethylamine Activation
作者:Caitlan E. Ayala、Andres Villalpando、Alex L. Nguyen、Gregory T. McCandless、Rendy Kartika
DOI:10.1021/ol301520d
日期:2012.7.20
Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.