1-Bromo-3-methylbutane → HCID 86615388, compound

Participants

Reaction Steps

Add (2R, 5R)-2-{(4S, 5S)-3-Acetyl-4-[3,5-difluoro-benzyl]-2,2-dimethyl-oxazolidin-5-yl}-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.06 g, 0.13 mmol) in 1.0 mL dimethylformamide to 60% sodium hydride (0.006 g, 0.15 mmol) in 0.5 mL dimethylformamide at room temperature and stir for 15 minutes. Add 1-bromo-3-methylbutane (0.023 mL, 0.19 mmol) and stir at room temperature overnight. Add 60% sodium hydride (0.006 g, 0.15 mmol) and 1-bromo-3-methylbutane (0.023 mL, 0.19 mmol) and stir for 4 h at room temperature. Quench with water and extract with diethyl ether, dry the organic layer over magnesium sulfate and concentrate. Subject the residue to silica gel chromatography, eluting with 100% dichloromethane to 90:10 dichloromethane: ethyl acetate to provide the desired compound (0.05 g, 75%).

Provenance & Evidence