(S)-benzyl 4-bromo-1-(3,5-dichlorophenyl)-3-oxobutan-2-ylcarbamate → HCID 86622360, compound

Participants

Reaction Conditions

Reaction Steps

Step BF (6): A 1M solution of LiAlH(OtBu)3 in THF (22.9 mL, 22.9 mmol) was diluted with THF (30.5 mL) and ethanol (56 mL) and cooled to −78° C. A solution of (S)-benzyl 4-bromo-1-(3,5-dichlorophenyl)-3-oxobutan-2-ylcarbamate (5.093 g, 11.45 mmol) in THF (56 mL) was then added dropwise down the side of the flask. After 15 min, TLC indicated no starting material remained. The reaction was carefully quenched with 1M HCl and let warm to rt. The organic solvents were removed in vacuo. The residue was taken up in EtOAc, and the aluminum salts removed via filtration. The organic layer was dried over MgSO4, and concentrated to afford benzyl (2S,3S)-4-bromo-1-(3,5-dichlorophenyl)-3-hydroxybutan-2-ylcarbamate (4.08 g, 80% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.05-7.50 (m, 9H) 5.55 (d, J=5.80 Hz, 1H) 4.99 (d, J=12.8 Hz, 1H) 4.87 (d, J=12.8 Hz, 1H) 3.66-3.77 (m, 1H) 3.56-3.65 (m, 2H) 3.36-3.45 (m, 1H) 3.01 (dd, J=13.73, 3.05 Hz, 1H) 2.59 (dd, J=13.43, 10.38 Hz, 1H).

Provenance & Evidence