N-Hydroxyphthalimide → HCID 14814200, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2,2-dimethyl-1,3-dioxolane-4-methanol (27 g, 0.2 mol), triphenylphosphine (53.5 g, 0.2 mol) and N-hydroxyphthalimide (33.3 g, 0.2 mol) in dry tetrahydrofuran (500 ml) cooled to 0° C. was added diethylazodicarboxylate (38.5 g, 0.22 mol). After stirring for 18 hours at 20° C. the originally dark red solution turned pale yellow and was then evaporated to dryness under reduced pressure. The residue was loaded onto a silica column in chloroform and eluted with hexane-acetone (3:1), yielding (R)-N-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)phthalimide as white plates (31.2 g, 55%), m.p. 100°-2° C. [α]D20 =+15.6° (C 0.98 in methanol); 1R: υmax (nujol) 1790, 1770, 1720, 1600 cm-1 ; 1H NMR: δH (CDCl3), 1.35 (3H, s, CH3), 1.41 (3H, s, CH3), 3.97 (1H, q, J=5.5, 8.8 Hz, CH2ON/CH2OC), 4.17 (2H, m, 1H of CH2ON+1H of CH2OC), 4.32 (1H, q, J=5.5, 10.0 Hz, CH2ON/CH2OC), 4.50 (1H, m, CH), 7.74-7.87 (4H, m, aromatic); m/z 262 (M+-CH3, 50%).

Provenance & Evidence