Triethylamine → (+)-trans-1-(3,4-Dichlorobenzamido)-2-acetoxy-7-(pyrrolidinoformamido)tetraline

Participants

Reaction Steps

A solution of pyrrolidine carboxamide (1.5 mL) in CH2Cl2 (25 mL) was treated with POCl3 (0.23 mL). After 1.5 h, the solution was treated with triethylamine (1 mL) and 115 (0.5 g). After stirring over night, the solvent was evaporated, the residue was treated with ice-water, the mixture neutralized, and the mixture extracted with EtOAc. The extracts were washed with brine and the solvent was dried and evaporated to give a dark oil. The oil was purified by radial chromatography eluting with 5% EtOH—CHCl3 to give a tan solid that was recrystallized from EtOAc to give a white solid (0.18 g), m.p. 229° C., dec.

Provenance & Evidence