tert-Butanol → tert-Butyl ((3-(3-bromophenyl)oxetan-3-yl)methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

2-[3-(3-Bromophenyl)oxetan-3-yl]acetic acid (840 mg, 2.789 mmol) was dissolved in tert-butanol (8 mL) and triethylamine (310.5 mg, 427.7 μL, 3.068 mmol) was added followed by diphenylphosphoryl azide (844.3 mg, 661.2 μL, 3.068 mmol). Heat at 80° C. for 4 hours. The reaction was allowed to cool and the solvent removed under reduced pressure. Ethyl acetate was added and the organic layer was washed with 5% citric acid soln, NaHCO3 (sat. aq. soln.) and brine. The organics were dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude product was pre-adsorbed onto silica and purified (Companion, 40 g) eluting with 2.5-50% EtOAc:Petrol ether to give tert-butyl N-[[3-(3-bromophenyl)oxetan-3-yl]methyl]carbamate as a white solid (433 mg, 45%).

Provenance & Evidence