Ethyl trifluoromethanesulphonate → HCID 131725727, compound

Participants

Reaction Steps

To a solution of (5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (5.0 g, 11.0 mmol) in THF (50 mL) at −78° C. was added LHMDS (1.0 M in THF, 12.6 mL, 12.6 mmol). The mixture was stirred for 30 min before ethyl triflate (1.78 mL, 1.25 equiv.) was added. The reaction was stirred between −78° C. to −40° C. for 45 min. It was quenched with 5% citric acid at −50° C., extracted with ethyl acetate. The combined organic phases were washed with 5% NaHCO3, brine, and dried over MgSO4NaHCO3, brine, and dried over MgSO4. Evaporation of the solvent and flash column chromatography (hexanes/EtOAc, 4:1) gave the desired product (90% yield) as viscous oil. 1HNMR (400 MHz, CDCl3) δ 7.63 (m, 4 H), 7.41 (m, 6 H), 4.13 (m, 2 H), 3.86 (m, 1 H), 3.74 (d, 1 H), 2.71 (m, 1 H), 2.24 (t, 1 H), 1.95 (m, 1 H), 1.78 (q, 1 H), 1.46 (s, 9 H), 0.95 (t, 3 H).

Provenance & Evidence