Tetrahydrofuran → 2-[3-(2,2-Dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol

Participants

Reaction Steps

6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinane (4.07 g, 10.03 mmol) was stirred in a 1M solution of tetrabutylammonium fluoride in THF (40 mL, 40 mmol) for 2 h at room temperature. Saturated aqueous NaHCO3 was added, and the reaction mixture was extracted with CHCl3. The organic layers were dried (Na2SO4), concentrated and the residue was filtered through a silica plug flushing with 1:1 hex:EtOAc to afford 2-[3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol in quantitative yield as a clear oil that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 37.45-7.37 (m, 4H), 7.31 (m, 1H), 5.51 (dd, 1H, J=10.9, 2.1 Hz), 4.69 (d, 1H, J=11.0 Hz), 4.30 (m, 1H), 3.58 (m, 2H), 2.99 (m, 1H), 2.31 (dt, 1H, J=14.1, 3.4 Hz), 2.16 (ddd, 1H, J=14.1, 11.7, 4.4 Hz), 2.04 (ddd, 1H, J=14.5, 7.0, 4.7 Hz), 1.92 (ddd, 1H, J=14.6, 6.9, 4.7 Hz), 1.28 (s, 9H).

Provenance & Evidence