Allyl bromide → (6S)-N-Phenyl-3-[3-(trifluoromethyl)benzyl(benzyloxycarbonyl)amino]-4-oxo-8beta-allyl-8-methyl-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6alpha-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 12c (2.155 g, 3.74 mmol) in 16 mL THF at −78° C., was added 1.0 M LIHMDS in THF (7.66 mL, 7.66 mmol). The mixture was stirred at −78° C. for 10 min, then allyl bromide (0.81 mL, 9.34 mmol) was added. The mixture was allowed to slowly warm to −40° C. and was maintained at this temperature for 30 min. The reaction was quenched with sat. NH4Cl, then diluted with EtOAc. The organic phase was washed with 0.5 M HCl and brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography (40% EtOAc/hexanes) to afford 1.101 g (48%) of 117a as a colorless gum. MS (ESI) 617.2 (M+H+).

Provenance & Evidence