反应详情

A mixture of 39h-b (170 mg, 300 μmol), acetone (871 μL, 11.9 μmol), acetic acid (69.1 μL, 1.20 mmol), and sodium triacetoxyborohydride (255 mg, 1.20 mmol) in dichloroethane (17 mL) was stirred at room temperature for 2 h. The reaction was diluted with EtOAc (500 mL), washed with saturated NaHCO3 (3×150 mL), water (2×100 mL), and brine (150 mL), dried over Na2SO4, filtered, and evaporated. The residue was purified by CombiFlash chromatography (silica, 0–10% MeOH/CH2Cl2) to provide (R*)-1-((1S*,2R*,4R*)-4-(isopropylamino)-2-(phenylsulfonylmethyl)cyclohexyl)-3-((2-(3-(trifluoromethyl)phenyl)-1,3-dioxolan-2-yl)methyl)pyrrolidin-2-one (39i-b, 106 mg, 58%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.89 (d, J=7.2 Hz, 2H), 7.68 (s, 1H), 7.64–7.39 (m, 6H), 4.20 (s, 1H), 4.05–3.90 (m, 2H), 3.81–3.60 (m, 3H), 3.48–3.11 (m, 4H), 3.10–2.88 (m, 1H), 2.60–2.10 (m, 5H), 2.09–1.60 (m, 8H), 1.43–1.00 (m, 6H); 19F NMR (282 MHz, CDCl3) δ −62.9; ESI MS m/z 609 [C31H39F3N2O5S+H]+.

1. washwashed with saturated NaHCO3 (3×150 mL), water (2×100 mL), and brine (150 mL)
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. customevaporated
5. customThe residue was purified by CombiFlash chromatography (silica, 0–10% MeOH/CH2Cl2)