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Sodium carbonate
Abstract
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A novel synthesis of estr-5(10)-en-6-ones is achieved by base-induced heterolytic fragmentation of 19-acetoxy-5α-bromo-6-oxosteroids in good yield.
A cleavage of N-tert-butyloxycarbonyl protection by Na2CO3 is reported. The N-free products are obtained in excellent yields. The compatibility of the method with the presence of acidic or basic groups is demonstrated. The reactions were performed on indole, azaindole, indazole, pyrazole, indolinone, quinolinone, and oxazolone.
[Structure: see text] A trichloroacetamide group was converted to an isocyanate, which was in situ captured by a variety of alcohols in the presence of CuCl and n-BuN4Cl to afford the corresponding carbamates. The scope and limitation of this transformation are also described.