Ammonia → [(2,2-Dimethyl-1,3-dioxan-5-yl)methyl](methyl)amine

Participants

Reaction Conditions

Reaction Steps

Methylamine solution (3 mL, 34.8 mmol) was added to a solution of (2,2-dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate (0.9 g, 4.01 mmol, prepared as per B. Xu et al. J. Med. Chem. 2002, 45, 5694) in DMSO (7 mL) and stirred at 75° C. overnight. The reaction was diluted with CHCl3 and the CHCl3 washed with water (×2), dried and concentrated in vacuo to afford approximately 670 mg of crude product. The crude material was columned on silica eluting with DCM, 20% MeOH/DCM, and 20% 7N NH3 in MeOH/DCM to afford (2,2-dimethyl-1,3-dioxan-5-yl)-N-methylmethanamine (330 mg, 52% yield) as an oily residue. 13C NMR (CD3OD) δ 99.7, 64.4 (2×CH2), 52.3, 36.9, 36.0, 26.0, 23.5.

Provenance & Evidence