Useful Reagents for Primary and Secondary Amine Synthesis

Fukuyama and co-workers have recently demonstrated the amination of alkyl halides and alcohols using the N-substituted sulfonamide 1.^1a) Smooth reactions of 1 occur with alkyl halides under basic conditions and alcohols under Mitsunobu conditions to provide o-nitrobenzenesulfonyl (o-Ns) amines 2. The various o-Ns amines (Alloc, Boc, Cbz) 2 obtained from these reactions can be deprotected, under the appropriate conditions, to afford the monoprotected amines 3 and 4. Furthermore, 3 can be converted to the primary amine 5 in high yields via a second deprotection. Compound 4 can be converted to the secondary amine 6 in high yields by repeating the alkylation and deprotection process.^1b)