Benzyl Bromide → HCID 117966886, compound

Participants

Reaction Steps

To a solution of (R)-1-(tert-butoxycarbonyl)-4,4-dimethyl-5-oxopyrrolidine-2-carboxylic acid (D38) (320 mg, 1.24 mmol) in acetone (10 ml), TEA (0.35 ml, 2.49 mmol) and benzyl bromide (0.23 ml, 1.86 mmol) were added and the resulting mixture was stirred at RT for 18 hrs. TEA (0.35 ml, 2.49 mmol) and benzyl bromide (0.23 ml, 1.86 mmol) were added and the reaction stirred for 24 hrs prior addition of further TEA (0.35 ml, 2.49 mmol) and benzyl bromide (0.23 ml, 1.86 mmol). The final mixture was then refluxed for 18 hrs. Solvents were evaporated off and the resulting residue was re-dissolved in EtOAc, washed with water (3×10 ml), dried over Na2SO4 and evaporated in vacuo to afford a residue that was purified by Biotage SNAP-Si column (25 g) eluting with a mixture DCM/EtOAc from 100/0 to 90/10. Collected fractions after solvent evaporation afforded the title compound (D39) (260 mg).

Provenance & Evidence