Ethanol → (R)-2-amino-2-(6-(4-propylcyclohexyloxy)naphthalen-2-yl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

(R)-4-methyl-4-(6-(4-propylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one (0.4786 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 that the reaction was complete. The reaction mixture was concentrated under vacuum. The product was dissolved in methylene chloride (5 mL) and washed with water (2×5 mL). The layers were separated (phase separator cartridge) and the organic layer was concentrated under vacuum and purified by HPLC to give 0.418 g of the title compound (9% yield). MS: m/z=325.35 [M-NH2]+. 1H NMR (400 MHz, MeOD) δ 0.95 (t, J=7.28 Hz, 3 H), 1.10-1.23 (m, 1 H), 1.25-1.33 (m, 2 H), 1.35-1.51 (m, 5 H), 1.57-1.74 (m, 3 H), 1.80 (s, 3 H), 1.87-1.95 (m, 1 H), 2.04-2.13 (m, 2 H), 2.21-2.28 (m, 1 H), 3.80-3.86 (m, 1 H), 3.91-3.97 (m, 1 H), 4.36-4.46 (m, 0.3 H), 4.73-4.78 (m, 0.7 H), 7.19 (dd, J=8.91, 2.38 Hz, 0.3 H), 7.24 (dd, J=8.91, 2.38 Hz, 0.7 H), 7.28 (d, J=2.26 Hz, 1 H), 7.53 (dd, J=8.78, 2.01 Hz, 1 H), 7.80-7.90 (m, 3 H)

Provenance & Evidence