4'-Hydroxyacetophenone → 4-acetylphenyl 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylate

Participants

Reaction Steps

At 0° C., 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylic acid (1.0 g) is dissolved in ethyl acetate (25 ml), dicyclohexylcarbodiimide (DCC; 1.26 g) is then added and the reaction mixture is subjected to agitation for 45 minutes at 0° C. Dimethylaminopyridine (DMAP; 100 mg) and 4′-hydroxyacetophenone (565 mg) are successively added, the reaction mixture is then left to return to room temperature. After 5 hours of agitation, the mixture is filtered and the filtrate is washed with a sodium hydrogen carbonate saturated solution, then with a sodium chloride saturated solution. The organic phase is dried on MgSO4, filtered and concentrated. The obtained orange oil is purified by chromatography on silica to obtain the desired product as a transparent oil (940 mg).

Provenance & Evidence