Triethylamine → HCID 18367229, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(1,4-dihydroxybutyl)-4,5-diphenyloxazole (1 g) in tetrahydrofuran (10 ml) were added methanesulfonyl chloride (1.6 g) and triethylamine (1.5 ml) at 0° C. The solution was diluted with ethyl acetate and washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated. The residue was dissolved in benzylamine (10 ml). After being stirred for 2 hours at 80° C., the mixture was partitioned between ether and water. The organic layer was washed with water and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to afford 1-benzyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine (1.3 g). MS (m/z): 381 (M+ +1) IR (Neat): 1600 cm-1NMR (CDCl3, δ): 1.8-2.6 (5H, m), 3.0-3.2 (1H, m), 3.60 (1H, d, J=13 Hz), 3.85 (1H, t, J=7.8 Hz), 3.89 (1H, d, J=13 Hz), 7.0-7.8 (15H, m)

Provenance & Evidence