N-Hydroxyphthalimide → (S)-N-(2,2-Dimethyl-1,3-dioxolan-4-ylmethoxy)phthalimide

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-2,2-dimethyl-1,3-dioxolane-4-methanol (7.3 g, 0.05 mol), N-hydroxyphthalimide (8.15 g, 0.05 mol) and triphenylphosphine (13.11 g, 0.05 mol) in tetrahydrofuran (200 ml) was cooled to 0° C. and stirred during the addition of diethyl azodicarboxylate (9.57 g, 0.066 mol). The dark red solution was stirred at 25° C. for 18 h when the colour had turned to pale yellow, and the solution was evaporated to dryness. The residue was extracted once with ether (200 ml) and the ether removed under reduced pressure. The residue was chromatographed in chloroform-hexane 10:1 affording (S)-N-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)phthalimide (10.5 g, 69%) as a white solid; m.p. 99°-100° C., [α]D25 -14.6° (0.4 in MeOH); υmax (KBr) [α]D25 1790, 1730 and 1610 cm-1 ; δH (CDCl3) 1.35(3H,S,CH3), 1.4 (3H,S,CH3), 3.99(1H,q,J5.5,8.8 Hz,CH2ON/CH2OCMe2), 4.17(2H,m,1H of CH2ON+1H of CH2OCMe2), 4.32(1H,q,J5.7,10.1 Hz,CH2ON/CH2OCMe2), 4.50(1H,m,CH) and 7.75-7.87(4H,m,aromatic). Found: C, 60.53; H, 5.46; N, 5.03%. C14H15NO5 requires C, 60.64; H, 5.45; N, 5.05%.

Provenance & Evidence