Potassium Hydroxide → HCID 58158373, compound

Participants

Reaction Steps

A solution of benzyl ((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methylcarbamate (200 mg, 589 μmol) and potassium hydroxide (992 mg, 1.77E+04 μmol) in isopropanol (8 mL) was heated under reflux for 2 h. Silica gel was added and the mixture was concentrated to dryness, then applied to a silica gel column and eluted with 5% MeOH/CH2Cl2, then 7% 7N NH3/MeOH in CH2Cl2 to give ((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methanamine (112 mg, 545 μmol, 93% yield) as a syrup. 1H NMR δ 3.96-3.83 (3H, m); 3.70 (1H, dd, J=9.9, 11.5 Hz); 2.83-2.73 (2H, m); 2.67-2.55 (2H, m); 2.18 (3H, s); 1.89-1.77 (1H, m); 1.44 (3H, s); 1.39 (3H, s). 13C NMR (CDCl3) δ 98.8, 72.9, 62.8, 41.9, 41.4, 38.5, 29.3, 20.2, 17.3.

Provenance & Evidence