Ethanol → HCID 178455815, compound

Participants

Reaction Conditions

Reaction Steps

(R)-4-[6-(cis-4-Ethyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.4603 g, 0.001302 mol) was dissolved in ethanol (5.00 mL, 0.0856 mol) in a capped 40 mL vial equipped with a magnetic stir bar. 4.2 M Lithium hydroxide, monohydrate in water (2.8 mL) was added and the mixture was heated overnight at 80° C. TLC analysis showed the reaction was complete. The mixture was concentrated to dryness under vacuum. Methylene chloride (5 mL) and water (5 mL) were added and the layers were separated by phase separator cartridge. The organic layer was dried with MgSO4, filtered, concentrated and purified by HPLC to give 0.038 g of the title compound (9% yield). MS: m/z=311.26 [M−NH2]+. 1H NMR (400 MHz, MeOD) δ 0.95 (t, J=7.15 Hz, 3H), 1.28-1.38 (m, 3H), 1.39-1.50 (m, 2H), 1.58-1.74 (m, 4H), 1.80 (s, 3H), 2.04-2.14 (m, 2H), 3.83 (d, J=11.55 Hz, 1H), 3.94 (d, J=11.55 Hz, 1H), 4.76 (br. s., 1H), 7.21-7.30 (m, 2H), 7.53 (dd, J=8.91, 1.88 Hz, 1H), 7.82-7.88 (m, 3H)

Provenance & Evidence