Triethylamine → HCID 86618880, compound

Participants

Reaction Conditions

Reaction Steps

1.27 ml of triethylamine and then (over 20 minutes) a solution of 1.60 g of sulphur trioxide-pyridine complex in 6 ml of dimethyl sulphoxide are added dropwise at 0° C. to the solution of 1.44 g of tert-butyl {1-hydroxymethyl-3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-4-methylpentyl}carbamate in 10 ml of dichloromethane. After 40 minutes, 10 ml of ice-water are added dropwise and the reaction mixture is stirred at 10° C. for a further 10 minutes. The reaction mixture is extracted with dichloromethane (3×)—the combined organic phases are washed successively with 10% aqueous sodium hydrogensulphate solution, water, 10% sodium hydrogencarbonate solution and brine, dried over magnesium sulphate and concentrated by evaporation. The crude title compound is obtained as a yellowish foam from the residue. Rf=0.73 (2:1 EtOAc-heptane). Rt=5.48 (gradient I).

Provenance & Evidence