Triphenylphosphine → HCID 54448135, compound

Participants

Reaction Steps

((1R)-2-(2-Naphthyl)-1-(phenethylcarbamoyl)ethyl)carbamic acid tert-butyl ester (2.20 g, 5.26 mmol) was dissolved in dry THF (50 ml). Triphenylphosphine (2.76 g; 10.52 mmol) diethylazodicarboxylate (1.66 g, 10.52 mmol) and trimethylsilyl azide (1.22 g; 10.52 mmol) were added. The mixture was stirred overnight at room temperature. Ammonium ceric nitrate (23.06 g; 21.04 mmol) was dissolved in water (400 ml) and added dropwise to the reation mixture. THF (120 ml) was added and the reaction mixture was extracted with methylene chloride (3×300 ml). The organic phase was dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was chromatographed on silica (5×40 cm) using ethyl acetate/heptane as eluent (1:1) to afford 0.30 g of ((1R)-2-(2-naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethyl)carbamic acid tert-butylester.

Provenance & Evidence