Oxygen → N-(2-hydroxymethylbutyl)-4-benzylpiperidine

Participants

Reaction Steps

A solution of diethylmagnesium (5 ml of a 0.8 M solution in diethyl ether, 4 mmol) was placed in a Schlenk tube and the solvent removed. The residue was dissolved in THF (1 ml). (Cyclopentadienyl)(1-[(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl]-4,5,6,7-tetrahydroindenyl)zirconium dichloride (prepared as in Example 1, 24 mg, 0.05 mmol) was added under positive argon flow followed by N-allyl-4-benzylpiperidine (0.215 g, 1 mmol) in THF (1 ml). The reaction mixture was stirred at room temperature overnight. The mixture was cooled to 0° C. and a balloon of oxygen gas added. The tube was flushed through with a small amount of oxygen and the reaction mixture was stirred overnight. The reaction mixture was poured into aqueous ammonium chloride solution (100 ml) and the aqueous was extracted with diethyl ether (3×50 ml). The organic extracts were combined, dried and evaporated to leave a residue which was purified by column chromatography (eluant 20% diethyl ether in petroleum ether) followed by Kugelrohr distillation (170° C., 1.0 mbar) to give the title compound as a clear oil which crystallised on standing (0.096 g, 37%, 42% ee).

Provenance & Evidence