Ethanol → (R)-2-amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propan-1-ol

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Reaction Steps

(R)-4-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-4-methyloxazolidin-2-one (30.0 mg, 0.0000679 mol) was dissolved in ethanol (2 mL, 0.03 mol) and water (0.8 mL, 0.05 mol) then lithium hydroxide (17 mg, 0.00072 mol) was added and was heated to reflux overnight. LCMS shows no SM and a new peak at 1.51 399.17 ([M−NH2]+, 100). After concentration, the residue was taken up into methylene chloride and water. The aqueous layer was extracted with methylene chloride and concentrated. Column chromatography with MeOH/methylene chloride gave (R)-2-amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propan-1-ol as a white solid (26.0 mg, 92%). LCMS 1.51 399.17 ([M−NH2]+, 100%). 1H NMR (400 MHz, MeOD) δ=7.95 (br. s., 1H), 7.89-7.76 (m, 3H), 7.64 (d, J=8.6 Hz, 1H), 7.43-7.20 (m, 7H), 6.98-6.87 (m, 3H), 5.00 (br. s., 2H), 3.84-3.77 (m, 1H), 3.77-3.69 (m, 1H), 1.60 (s., 3H).

Provenance & Evidence