Isobutanol → 1-[4-(4-Isobutoxymethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]-ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of isobutyl alcohol (0.54 mL, 5.8 mmol) in THF (5 mL) is cooled to 0° C. and treated with sodium bis(trimethylsilyl)amide (5.8 mL of a 1 M solution in THF, 5.8 mmol) and stirred for 1 h. A solution of 1-[4-(4-chloromethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]-ethanone (1.69 g, 5.3 mmol), prepared as in Part B, in THF (30 mL) is added dropwise, and the mixture is allowed to warm to 23° C., and stirred for 18 h. The reaction mixture is partitioned between EtOAc (150 mL) and H2O (75 mL), and the organic layer is washed with brine (1×100 mL), dried (MgSO4), and concentrated. The residue is purified by chromatography on silica using EtOAc as eluent to afford the title compound as a yellow oil.

Provenance & Evidence