Benzyl Bromide → HCID 178454132, compound

Temperature

0 °C

tert-Butyl(trans-3-hydroxycyclobutyl)carbamate (0.93 g, 4.97 mmol) was dissolved in dry THF (20 mL) under a nitrogen atmosphere, and the solution cooled to 0° C. To this clear solution, sodium hydride (60% dispersion in oil, 0.2 g, 4.97 mmol) was added portion wise (evolution of H2 observed). The mixture was stirred at RT for 30 min then benzyl bromide (0.88 mL, 7.45 mmol) added dropwise and the resulting dark brown suspension stirred at rt for 16 h. The reaction mixture was quenched with saturated aqueous NH4Cl (20 mL) and partitioned between saturated aqueous NaHCO3 (40 mL) and DCM (60 mL). The combined organic fractions were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient 0-50% EtOAc in cyclohexane) to afford the title compound as a off-white solid (0.99 g, 72%). 1H NMR (CDCl3, 400 MHz): δ 7.35-7.31 (5H, m), 4.65 (1H, br, NH), 4.40 (2H, s), 4.24-4.12 (2H, m), 2.50-2.35 (2H, m), 2.18-2.06 (2H, m), 1.43 (9H, s).

1. stirringthe resulting dark brown suspension stirred at rt for 16 h
2. customThe reaction mixture was quenched with saturated aqueous NH4Cl (20 mL)
3. custompartitioned between saturated aqueous NaHCO3 (40 mL) and DCM (60 mL)
4. washThe combined organic fractions were washed with brine (20 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by column chromatography (gradient 0-50% EtOAc in cyclohexane)

ORD record

ord-dcc60984a712491a88c49ab78df92a25

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2