Methanol → Methyl 2-(4-hydroxy-1,2-oxazolidine-2-carbonyl)benzoate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.28 ml) was added to a solution of N-hydroxyphthalimide (5.00 g) and (R)-(+)-epichlorohydrin (2.40 ml) in anhydrous dioxane (10 ml) under nitrogen. The mixture was stirred at 50° C. for 48 h, further (R)-(+)-epichlorohydrin (0.24 ml) and triethylamine (0.28 ml) were added and stirring continued at 50° C. for 24 h. Methanol (10 ml) and further triethylamine (4.27 ml) were added and stirring continued at 50° C. for 2 h. The mixture was evaporated under reduced pressure, the residue dissolved in saturated aqueous sodium bicarbonate solution (100 ml) and extracted with ethyl acetate (6×100 ml). Combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate to give the sub-title compound (3.4 g). MS(ESI) 252 [M+H]+. δ 1HCDCl3 3.66 (1H, d, br), 3.79 (1H, d, br), 3.89-3.99 (1H, m), 3.99-4.10 (1H, m), 4.74-4.81 (1H, m), 7.46 (1H, d), 7.49 (1H, t), 7.62 (1H, t), 7.99 (1H, d).

Provenance & Evidence