Methylhydrazine → HCID 21650354, compound

Participants

Reaction Steps

Methylhydrazine (0.97 ml, 18 mmol) was added to a solution of diethyl [4-(t-butyldimethylsilyloxy)-3-(phthalimidooxy)butyl]phosphonate (5.9 g, 12 mmol) in dichloromethane (40 ml). A white solid separated after a few minutes. The mixture was stirred overnight, filtered, the solvent evaporated and the residue chromatographed on silica gel using dichloromethane-methanol (98:2) as eluant. The title compound was obtained as a colorless oil (3.05 g, 70%). IR: υmax (film). 3320, 2970, 2940, 2860, 1595, 1470, 1390, 1250, 1160, 1060, 1030, 960, 840, 780, cm-1. 1H NMR: δH (CDCl3) 0.08 (6H, s, SiMe2), 0.9 (9H, s, SiBut), 1.3 (6H, t, J=7Hz, (OCH2CH3)2), 1.5-2.2 (4-H, m, CH2CH2P), 3.4-3.9 (3H, m, OCH2CH), 4.15 (4H, m, (OCH2CH3)2), 5.3 (2H, broad, D2O exchangeable NH2).

Provenance & Evidence