Ethanol → (2R)-2-amino-2-(6-(spiro[5.5]undecan-3-yloxy)-5-(trifluoromethyl)naphthalen-2-yl)propan-1-ol

Participants

Reaction Steps

The mixture of (4R)-4-methyl-4-(6-(spiro[5.5]undecan-3-yloxy)-5-(trifluoromethyl)naphthalen-2-yl)oxazolidin-2-one (62.5 mg, 0.000135 mol) and lithium hydroxide (36 mg, 0.0015 mol) in ethanol (2 mL, 0.04 mol) and water (0.7 mL, 0.04 mol) was heated to reflux for overnight. The solvent was removed under vacuum and the residue was partitioned between water/CH2Cl2. The aqueous was extensively extracted with CH2Cl2. And the combined organic phase was dried over Na2SO4. The concentrated residue was taken up into methylene chloride and subjected to chromatography purification with MeOH/CH2Cl2 (10:90 to 80:20) to give (2R)-2-amino-2-(6-(spiro[5.5]undecan-3-yloxy)-5-(trifluoromethyl)naphthalen-2-yl)propan-1-ol as a white gel (39.0 mg, 66%). LCMS: Rf=1.86 min 419.30 ([M−16], 100%). 1H NMR (400 MHz, MeOD) δ=8.15 (dd, J=1.9, 9.2 Hz, 1H), 8.07 (d, J=9.2 Hz, 1H), 7.96 (d, J=2.1 Hz, 1H), 7.71 (dd, J=2.2, 9.3 Hz, 1H), 7.47 (d, J=9.3 Hz, 1H), 4.68-4.59 (m, 1H), 3.76 (d, J=10.8 Hz, 1H), 3.70 (d, J=10.8 Hz, 1H), 1.95-1.83 (m, 2H), 1.82-1.67 (m, 4H), 1.54 (s, 3H), 1.53-1.42 (m, 8H), 1.42-1.28 (m, 4H).

Provenance & Evidence