1-cyclobutyl-N-methylmethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: For example, methyl 3-amino-2-diphenylmethoxybenzoate A28.8 is reacted, as described above, with 2-bromo-4-methylpyridine-3-carboxaldehyde A28.9 (Arkivoc, 2000, 1, 52) to produce after cyclization, the tricyclic ester A28.10. The ester is then reacted with trimethylaluminum and N-methylcyclobutylmethylamine A28.11 to give 9-benzhydryloxy-4-methyl-benzo[b][1,8]naphthyridine-8-carboxylic acid cyclobutylmethyl-methyl-amide A28.12. Benzylic bromination then gives the bromomethyl analog A28.13. The latter compound is heated at 120° C. with excess of a trialkyl phosphite to produce after deprotection the phosphonate A28.14. is reacted to produce after cyclization