Triethylsilane → HCID 16659482, compound

Participants

Reaction Conditions

Reaction Steps

(2R)-2-[2-Fluoro-4-nitro(2,2,2-trifluoroethyl)anilinol-3-methyl-1-butanol (Structure 38 of Scheme VIII, where R4=isopropyl, Rx=CF3. To a solution of (4R)-3-(2-fluoro-4-nitrophenyl)-4-isopropyl-2-trifluoromethyloxazolidine (1.8 g, 5.6 mmol) and Et3SiH (1.88 g, 16.1 mmol) in 15 mL CHCl3 was added TiCl4 (6 mL of a 1M solution in CH2Cl2, 6 mmol) at −78° C. The solution was stirred for 2 h, then allowed to warm to 0° C. and stirred for 2 h. The mixture was poured into 150 mL water and neutralized with 6N NaOH. The aqueous layer was extracted with CHCl3 (3×100 mL), and the combined organic layers washed with brine (150 mL), dried over MgSO4, filtered and concentrated. Flash chromatography (gradient elution, hexanes:EtOAc 9:1 to 3:1) afforded 1.6 g (88%) of (2R)-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-3-methyl-1-butanol, an orange oil. Data for (2R)-2-[2-fluoro-4-nitro(2,2,2-trifluoroethyl)anilino]-3-methyl-1-butanol: Rf 0.3 (3:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.96 (dd, 1H, J=8.8, 2.3), 7.92 (dd, 1H, J=13.4, 2.5), 7.37 (dd, 1H, J=8.8, 8.8), 4.33-4.23 (m, 1H), 4.03-3.86 (m, 2H), 3.81-3.74 (m, 1H), 3.36-3,27 (m, 1H), 1.97-1.88 (m, 1H), 1.85 (broad s, 1H), 0.99 (d, 3H, J=6.6), 0.94 (d, 3H, J=6.6).

Provenance & Evidence