Methylhydrazine → HCID 14814232, compound

Participants

Reaction Steps

A solution of (R)-N-(1,4-dibenzyloxybut-2-oxy)phthalimide (0.6 g, 1.3 mmol) in dichloromethane (5 ml) was treated with methylhydrazine (86 μl, 1.6 mmol). A deep red colouration developed, disappearing gradually as a white solid precipitated out of solution. After stirring at room temperature for 30 minutes additional methylhydrazine (8 μl, 0.15 mmol) was added. The mixture was stirred at room temperature for an additional 30 minutes, filtered and the filtrate washed with 3% sodium carbonate solution (5 ml). The organic phase was dried (MgSO4), the solvent removed under reduced pressure and the residue chromatographed on silica eluting with ethyl acetate-hexane to give (R)-1,4-dibenzyloxybut-2-oxyamine (0.32 g, 77%), [α]D25 +10.1° (c 0.14 in ethanol); IR: υmax (film) 3310, 3250, 3090, 3060, 3030, 2920, 2860, 1585, 1495, 1450, 1365, 1310, 1200, 1100, 1030, 950, 915, 740, 700 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), 4.45 (2H, s, CH2), 5.36 (2H, s, D2O exchangeable NH2) 7.35 (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). M+ observed 301.1670; C18H23NO3 requires M+ 301.1678.

Provenance & Evidence