Water → HCID 66953648, compound

Participants

Reaction Steps

To a solution of benzyl ((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methylcarbamate (82 mg, 242 μmol) in dry THF (1.5 mL) was added lithium aluminium hydride 2.0 M in THF (1208 μl, 2416 μmol) and the solution was stirred at RT for 18 h. Then water (0.12 mL), 15% NaOH (0.12 mL) and water (0.36 mL) were added carefully. The resulting mixture was filtered, the solids were washed with warm EtOAc and the filtrate was concentrated to dryness. Chromatography (5% MeOH in CH2Cl2, then 5% 7N NH3/MeOH in CH2Cl2) gave 1-((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)-N-methylmethanamine (30 mg, 137 μmol, 56.6% yield) as a syrup. 1H. NMR (CDCl3) δ 3.94-3.80 (2H, m); 3.69-3.62 (2H, m); 2.82 (1H, dd, J=2.9, 13.8 Hz); 2.64 (1H, dd, J=6.9, 13.8 Hz); 2.55 (1H, dd, J=4.7, 12.0 Hz); 2.44-2.38 (1H, m); 2.39 (3H, s); 2.18 (3H, s); 2.01-1.90 (1H, m); 1.44 (3H, s); 1.39 (3H, s). 13C NMR (CDCl3) δ 99.1, 73.9, 63.6, 51.8, 39.5, 38.7, 37.5, 29.6, 20.3, 17.6.

Provenance & Evidence