Reaction Steps
A solution of (S)-N-(1,4-dibenzyloxybut-2-oxy)phthalimide (5 g, 11.6 mmol) in dichloromethane (50 ml) was treated with methylhydrazine (0.8 ml, 15 mmol). A deep red colouration developed, disappearing gradually as a white solid precipitated out of solution. After stirring at room temperature for 1 hour, the solid was filtered off and the filtrate was washed with a 3% sodium carbonate solution. After drying (MgSO4) the solution was evaporated to dryness and the residual oil was chromatographed on silica eluting with ethyl acetate-hexane 5:1 to give (S)-1,4-dibenzyloxybut-2-oxyamine (2.66 g, 76%), [α]D25 -3.2° (c 0.3 in ethanol); IR: υmax (film) 3315, 3248, 3087, 3062, 3030, 2922, 2861, 1588, 1496, 1454, 1365, 1205, 1101, 1028, 738, 698 cm-1 ; 1H NMR: δH (CDCl3) 1.85 (2H, m, CH2), 3.55 (4H, m, 2×CH2), 3.90 (1H, m, CH), 4.49 (2H, s, CH2), 4.55 (2H, s, CH2), 5.36 (2H, s, D2O exchangeable NH2), 7.30 (10H, m, 2×C6H5); m/z 302 (MH+), 301 (M+, 3%), 181 (5), 163 (10), 106 (15), 105 (5), 92 (15), 91 (100), 71 (15), 65 (10). Found: C, 71.40; H, 7.66, N, 4.61%, M+ 301.1670. C18H23NO3 requires: C, 71.73; H, 7.69, N, 4.65% M+ 301.1678.
