Triethylamine → HCID 131731731, compound

Participants

Reaction Steps

A solution of benzyl[(2R,3S)-3-fluoro-1-hydroxypentan-2-yl]carbamate (2.4 g) in chloroform (40 mL) was cooled in ice, triethylamine (2 mL) and methanesulfonyl chloride (0.8 mL) were added thereto, and the mixture was stirred for 30 min. Saturated sodium hydrogen carbonate was added thereto, followed by extraction with chloroform and drying over anhydrous magnesium sulfate. After the desiccant was filterred off, the solvent was distilled off under reduced pressure, and the residue was dissolved in DMF (40 mL). Sodium azide (3.06 g) was added thereto, and the mixture was stirred at 60° C. for 2 hr. Water was added thereto, the resulting mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was dissolved in THF (50 mL), triphenylphosphine (3.59 g) and water (10 mL) were added thereto, and the resulting mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=98:2-80:20) to afford benzyl[(2R,3S)-1-amino-3-fluoropentan-2-yl]carbamate (2.34 g).

Provenance & Evidence