Water → HCID 86724639, compound

Participants

Reaction Steps

To olefin 16 (903.4 mg, 2.53 mmol) in THF (25 mL) under N2 was added NMO (60% wt solution in H2O, 0.90 mL, 5.06 mmol) and OsO4 (4% wt solution in H2O, 1.50 mL, 0.25 mmol). The solution was stirred at ambient temperature for 16 h, and NaIO4 (2.16 g, 10.12 mmol) was then added, followed by H2O (2.7 mL). Stirring was continued for 4 h, and the reaction mixture was then diluted with EtOAc (200 mL) and washed with 10% Na2S2O3 (4×50 mL). The combined washings were extracted with EtOAc (50 mL). The organic solutions were combined and washed with 5 M NaCl (20 mL) and dried, and the solvent was evaporated. The residue was separated by chromatography (silica gel, 30 g; 9:1 hexane-EtOAc) and led to 0.632 g (70%) of 18 as a colorless solid: mp 127-128° C.; Rf0.19 (95:5 hexane-EtOAc); [α]23D−39.0 (c 1.05, CH3OH); 1H NMR δ 7.92 (2H, dd, J=7.5 and 1.3 Hz), 7.60 (1H, tt, J=7.5 and 1.3 Hz), 7.49 (2H, t, J=7.6 Hz), 7.03 (1H, br d, J=6.7 Hz), 4.72 (1H, dd, J=7.4 and 4.8 Hz), 4.13 (1H, m), 1.49 (9H, s), 1.36 (3H, d, J=7.2 Hz); 13C NMR δ 200.0, 168.3, 156.9 (q), 135.5, 133.6, 128.8, 128.4, 83.8, 55.0, 42.9, 27.8, 14.2; MS APCI+ m/z 360.1417 [M+H]+ (calcd for C17H21F3NO4, 360.1423); anal. C, 56.39%, H, 5.60%, N, 3.96%, calcd for C17H20F3NO4, C, 56.82%, H, 5.61%, N, 3.90%.

Provenance & Evidence