[C:1]([S@@:5]([N:7]=[C:8]([C:14]([CH3:18])([CH3:17])[CH2:15][F:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].C1COCC1>C1COCC1>[CH3:4][C:1]([CH3:2])([S@@:5]([NH:7][C@@H:8]([C:14]([CH3:18])([CH3:17])[CH2:15][F:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6])[CH3:3]To a solution of (S)-ethyl 2-(tert-butylsulfinylimino)-4-fluoro-3,3-dimethylbutanoate (1.1 g, 3.94 mmol) in THF (8 mL) was added L-Selectride/THF (5.12 mL, 5.12 mmol) via a syringe pump at 6 mL/h rate at −78° C. The reaction mixture was stirred at −78° C. for 4 h after the completion of addition. The reaction was quenched by addition of aq. NH4Cl at −78° C., diluted with EtOAc and washed with water, brine, dried (MgSO4), concentrated and purified on silica gel chromatography (EtOAc/hexane) to afford (S)-ethyl 2-((S)-1,1-dimethylethylsulfinamido)-4-fluoro-3,3-dimethylbutanoate (0.38 g). 1H NMR (400 MHz, MeOD-d4) δ ppm 4.20-4.44 (4H, m), 3.99 (1H, s), 1.35 (3H, t, J=7.15 Hz), 1.13 (6H, dd, J=15.81, 2.01 Hz).
読み込み中…
