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

Participants

Reaction Conditions

Reaction Steps

(R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one (0.3672 g, 0.0009284 mol) was dissolved in ethanol (5.00 mL, 0.0856 mol) in a capped 40 mL EPA vial equipped with a stir bar. 4.2 M Lithium hydroxide, monohydrate in water (2.00 mL) was added and the mixture was heated at 80° C. overnight. TLC analysis showed that the reaction was complete. The mixture was concentrated to dryness 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 to dryness and purified by HPLC to give 0.467 g of the title compound (14% yield). MS: m/z=353.36 [M−NH2]+. 1H NMR (400 MHz, MeOD) δ 0.90-0.98 (m, 3H), 1.10-1.24 (m, 1H), 1.26-1.54 (m, 8H), 1.58-1.74 (m, 2H), 1.80 (s, 3H), 1.86-1.95 (m, 2H), 2.03-2.13 (m, 2H), 2.20-2.29 (m, 2H), 3.80-3.87 (m, 1H), 3.91-3.97 (m, 1H), 4.36-4.79 (m, 1H, 1:1 ratio), 7.17-7.26 (m, 1H, 1:1 ratio), 7.28 (d, J=2.51 Hz, 1H), 7.53 (dd, J=8.78, 2.01 Hz, 1H), 7.80-7.90 (m, 3H)

Provenance & Evidence