Sodium Chloride → triBoc Spermine Ethyl Acetate

Participants

Reaction Steps

2.6 ml of triethylamine (18.4 mmol, 2.5 eq) is added to a solution of 3.96 g of triBoc spermine (7.3 mmol, 1 eq) in 100 ml of acetonitrile. 0.81 ml of ethyl bromoacetate (7.3 mmol, 1 eq) is then quickly added to this solution under stirring. After 5 h of stirring at room temperature, the reaction medium is dumped into a saturated NaCl solution (100 ml) and extracted with ethyl acetate (2*100 ml). After the organic phases are dried, filtered and evaporated, the residue obtained is purified by flash chromatography on SiO2 (elution with a gradient from pure heptane to pure CH2Cl2, then with 90/10 CH2Cl2/MeOH). 2.77 g of a colorless oil is obtained (Yield=64%; TLC Rf=0.57; 90/10 CH2Cl2/MeOH) and 1.05 g of the starting triBoc spermine is recovered (adjusted yield=87%).

Provenance & Evidence