Methylamine → tert-butyl (S)-3-cyclopentyl-1-(methylamino)propan-2-ylcarbamate

Participants

Reaction Steps

A mixture of crude tert-butyl (S)-3-cyclopentyl-1-(methanesulfonyloxy)propan-2-ylcarbamate in ethanolic methylamine (30 mL) was heated under reflux overnight. The solvent was removed in vacuo and the residue was purified by silica chromatography to obtain tert-butyl (S)-3-cyclopentyl-1-(methylamino)propan-2-ylcarbamate (900 mg, 43% for 3 steps from) as a solid (900 mg, yield 43% for 3 steps from tert-butyl (S)-3-cyclopentyl-1-(t-butyldimethyl-silyloxy)propan-2-ylcarbamate). 1H NMR (CDCl3, 400 MHZ) δ 1.10 (m, 2 H), 1.44 (s, 9 H), 1.49 (m, 3 H), 1.60 (m, 3 H), 1.81 (m, 3 H), 2.69 (s, 3H), 2.90 (m, 1 H), 3.17 (m, 1 H), 3.92 (brs, 1 H), 5.66 (brs, 1 H).

Provenance & Evidence