Methanol → HCID 16659481, compound

Participants

Reaction Steps

To a solution of (4R)-3-(2-fluoro-4-nitrophenyl)-4-ethyl-2-trifluoromethyloxazolidine (9.2 g, 29.8 mmol) and Et3SiH (19.1 mL, 119 mmol) in 100 mL chloroform was added BF3OEt2 (7.56 mL, 60 mmol). The reaction was heated to reflux for 12 hrs, whereupon additional BF3OEt2 (7.56 mL, 60 mmol) was added, and the mixture heated at reflux for an additional 12 hrs. After cooling, MeOH (5 mL) was added and the reaction was allowed to stir at r.t. for an hour. The reaction was poured in water (250 mL) and extracted with ethyl acetate (3×250 mL). The organic layers were combined, washed sequentially with water (250 mL) and brine (250 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to a brown oil. Flash chromatography (gradient elution, hexanes:ethyl acetate 95:5 to 50:50) afforded 5.4 g (59%) of (2R )-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-1-butanol. Data for (2R )-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-1-butanol: 1H NMR (500 MHz, CDCl3) δ 7.98 (dd, J=8.8, 2.4, 1H), 7.94 (dd, J=13,2, 2.9, 1H), 7.37 (dd, J=8.8, 8.8, 1H), 4.12 (m, 1H), 3.87 (m, 1H), 3.77 (m, 1H), 3.70 (m, 1H), 3.57 (m, 1H), 1.78 (dd, J=6.8, 4.4, 1H), 1.58 (dq, J=7.8, 2.9, 2H), 0.95 (t, J=7.3, 1H).

Provenance & Evidence