Borane → HCID 68434406, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxazole (1 g, 14 mmol) in anhydrous THF (10 ml) was added borane. THF complex (14 ml, 1M in THF, 14 mmol) and the mixture stirred for 1 h, after which time the reaction was cooled to −78° C. and nBuLi (9 ml, 1.6 M in hexanes, 14 mmol) added dropwise and the reaction stirred for a further 1 h. A solution of Boc-piperidone (3.2g, 16 mmol) in THF (10 ml) is then added, the reaction stirred for a further 4 h at −78° C. before allowing the reaction to reach room temperature overnight. The solvent is then evaporated, the residue redissolved in EtOAc, washed with saturated ammonium chloride solution, dried (Na2SO4) and concentrated. Purification by flash column chromatography (EtOAc:Heptane 3:7) affords the title product (1.9 g, 44%) as a colourless gum, contaminated with an unknown byproduct. MS: 269.2 (MH+)

Provenance & Evidence