Abstract
N -Chlorination of various amides, carbamates and lactams with inexpensive and stable calcium hypochlorite on moist alumina proceeds smoothly and efficiently, e.g. the technically important 1-chlorohexahydroazepin-2-one (3 -Cl) and 1-chloropyrrolidin-2-one (7 -Cl) were obtained in 95% and 98% yield, respectively. Excellent results were also observed for the N -chlorination of protected amino acid esters with a cyclopropane moiety to give derivatives such as methyl (tert -butoxycarbonylchloroamino)cyclopropylacetate (1 -Cl), methyl (benzyloxycarbonylchloroamino)cyclopropylacetate (2 -Cl), methyl 1-(tert -butoxycarbonylchloroamino)cyclopropanecarboxylate (5 -Cl) and methyl trans -2-(tert -butoxycarbonylchloroamino)cyclopropanecarboxylate (6 -Cl) in 99%, 96%, 90% and 97% yield, respectively.
Key words
amides - amino acids -
N -chlorination - calcium hypochlorite - alumina
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