Water → (2S,3S)-2-(3,5-Bis-trifluoromethyl-benzyloxy)-3-phenyl-morpholine

Participants

Reaction Steps

A mixture of 0.68 g of 4-benzyl-2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenylmorpholine and 280 mg of 10% Pd/C in 36 ml of 97:3 ethanol:water was stirred under one atmosphere of hydrogen for 15 hr. The mixture was filtered through Celite, the filter cake was washed generously with ethanol, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on 68 g of silica eluting with 1 L of 33:67 hexanes:diethyl ether, then 1 L of 25:75 hexanes:diethyl ether to give 0.443 g (80%) of an oil, which by 1H NMR was pure cis morpholine. 1H NMR (400 MHz, CDCl3) δ 1.8 (1H, br s), 3.10 (1H, dd, J=12.5, 2.9 Hz), 3.24 (1H, td, J=12.2, 3.6 Hz), 3.62 (1H, dd, J=11.3, 2.5 Hz), 4.04 (1H, td, J=11.7, 3 Hz), 4.11 (1H, d, J=2.4Hz), 4.49 (1H, d, J=13.5 Hz), 4.74 (1H, d, J=2.5 Hz), 4.80 (1H, d, J=13.3 Hz), 7.25-7.40 (5H, m), 7.40 (2H, s), 7.68 (1H, s). Anal. Calcd. For C19H17F6NO2 : C, 56.30; H, 4.23; N, 3.46; F, 28.12. Found: C, 56.20; H, 4.29; N, 3.34; F, 27.94.

Provenance & Evidence