1,4-Cyclohexadiene → HCID 10799151, compound

Participants

Reaction Steps

To a flask containing 10% palladium on carbon (3.79 g) under nitrogen was added [2-[[2-(diethoxyphosphinyl)ethyl]amino]ethyl]carbamic acid phenylmethyl ester (3.79 g, 10 mmol) in ethanol (50 mL), followed by 1,4-cyclohexadiene (10.4 mL, 110 mmol). After stirring the suspension overnight, it was filtered through Celite®, preadsorbed onto silica gel, and purified by flash chromatography (7 cm diameter, elution with dried (MgSO4) 5/10/85 ammonium hydroxide/methanol/dichloromethane) to afford [2-[(2-aminoethyl)amino]ethyl]phosphonic acid diethyl ester as a yellow oil (1.98 g, 88%); MS (+FAB): 225 (MH+, 9), 194 (100), 166 (34), 138 (71), 120 (38), 57 (39), 44 (32); 1H NMR (CDCl3, 400 MHz): δ 4.18-4.04 (m, 4H), 2.91 (d of t, J=15 and 7 Hz, 2H), 2.80 (t, J=5.5 Hz, 2H), 2.68 (t, J=5.5 Hz, 2H), 1.98 (d of t, J=18 and 7 Hz, 2H), 1.68 (br s, 3 NH), 1.33 (t, J=7 Hz, 6H).

Provenance & Evidence