SYNTHESIS OF 3'-N-METHYLBIOTIN

Treatment of N, N′-dibenzylurea VII with sodium in liquid ammonia removed the benzyl group in the sterically more crowded environment to give the monobenzyl derivative VIII. The benzyl group which was removed was defined by conversion of VIII to an aldehyde derivative IX, in which the NH group formed had interacted with an aldehyde group generated in the side chain. The monobenzyl derivative VIII methylated on nitrogen and converted to 3′-N-methylbiotin by reactions analogous to those used in the synthesis of biotin itself. © 1978, American Chemical Society. All rights reserved.