Triethylamine → HCID 66621383, compound

Participants

Reaction Steps

A mixture of 3-(aminoethyl)benzyl alcohol (2.3 grams, 0.015 mol, 1 molequivalent), N,N′-bis(tert-butoxycarbonyl)-S-methylisothiourea (4.8 grams, 0.016 mol, 1.1 molequivalent), mercury chloride (4.5 grams, 0.016 mol, 1.1 molequivalent), and triethylamine (7 ml, 0.048 mol, 3 molequivalent) in dry DMF (25 ml) was stirred at room temperature overnight under nitrogen atmosphere. Ethyl acetate (100 ml) was then added and the suspension was filtered over Celite. The filtrate was washed with water, saturated aqueous NH4Cl, and brine, dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography (using a gradient eluent of a 10:90 to 30:70 mixture of EtOAc:hexanes), to give 1.9 grams (32%) of the pure product.

Provenance & Evidence