Diethyl Ether → Benzylurea

Participants

Reaction Conditions

Reaction Steps

Silyl lactam 1 was dissolved in dry THF (6 mL) and cooled to -78° C. To this solution was then added LDA and the reaction was stirred for 30 minutes at -78° C. after which time benzyl bromide was added via syringe. The reaction was stirred at -78° C. until reaction was complete (1.5 hours, TLC (1:9, ether:CH2Cl2) Rf (st mat.)=0.29. Rf(silyl-prod)=0.62. Rf(BzBr)=0.79). The reaction was then quenched at -78° C. with 6 uL water and then TBAF (1M in THF was added and the reaction was warmed to room temperature and stirred for 3 hours (TLC (1:9, ether:CH2Cl2) Rf(prod)=0.28). The reaction was partition betweem H2O/EtOAc and the organic layer was washed with with water and brine, dried (MgSO4) and filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (10% ether/CH2Cl2) to yield benzyl product 2 (71 mg, 48%).

Provenance & Evidence