Tetrahydrofuran → (R)-4-{6-[4-(1,1-dimethylpropyl)-cyclohexyloxy]-naphthalen-2-yl}-4-methyloxazolidin-2-one

Participants

Reaction Steps

To a mixture of (R)-4-(6-hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (Example 4, 300.0 mg, 1.233 mmol) and 4-(1,1-dimethyl-propyl)-cyclohexanol (252 mg, 1.48 mmol) in tetrahydrofuran (5 mL, 60 mmol) was added triphenylphosphine polymer-bound (1.07 g, 1.97 mmol). After the mixture was stirred at room temperate for 10 min, diisopropyl azodicarboxylate (0.388 mL, 1.97 mmol) was added dropwise. The mixture was stirred at room temperate for 48 hrs. The insoluble material was passed over a CELITE™ bed and washed with ethyl acetate. After the solvent was concentrated, the residue was purified with silica gel column eluted with ethyl acetate in hexanes from 0 to 40% to give 410 mg of white precipitate (R)-4-{6-[4-(1,1-dimethylpropyl)-cyclohexyloxy]-naphthalen-2-yl}-4-methyloxazolidin-2-one (84% yield). MS: m/z=396.30 M+H.

Provenance & Evidence