反应详情

The formylated 2-pyridone 2 (100 mg, 0.239 mmol) was dissolved in tetrahydrofuran (3.30 mL) at 0° C. Then 2M BH3.DMS.THF (0.131 mL, 0.262 mmol) was added dropwise during 15 min. The mixture was then stirred in room temperature during 1 h, quenched with methanol and concentrated twice from methanol. The residue was purified through flash column chromatography (CH2Cl2:MeOH, 9:1). Co-concentration from CH2Cl2 (×2) resulted in 4 as white foam (80.6 mg, yield: 80%). 1H-NMR (400 Mhz, CDCl3) δ 8.16 (d, J=8.23 Hz, 1H, ArH), 7.87 (d, J=7.96 Hz, 1H, ArH), 7.71 (d, J=8.14 Hz 1H, ArH), 7.64-7.48 (m, 2H, ArH) 7+(m, 1H, ArH) 6.83 (d, J=6.95 Hz, 1H, ArH), 5.68 (d, J=7.04 Hz, 1H, CHCO2Me), 4.72 (d, J=16∞Hz, 1H, Nph-CH2), 4.61 (d, J=16.28 Hz, 1H, Nph-CH2) 4.58-4∓(m, 2H, CH2OH) 3.84 (s, 3H, CH3) 3.76-3.62 (m, 2H, SCH2, OH) 3.60-3.50 (m, 1H, SCH2) 1.46-1.34 (m, 1H, CH-cyclopropyl) 0.65 (ss, 2H, CH2-cyklopropyl) 0.51 (ss, 2H, CH2-cyklopropyl) 13C-NMR (100 Mhz, CDCl3) δ 168.61, 161.87, 152.08, 146.62, 134.11, 133.76, 131.77, 128.94, 127.17, 126.37, 125.92, 125.66, 125.63, 124.26, 122.98, 114.93, 63.27, 58.78, 53.40, 31.77, 31.58, 11.81, 7.53, 7.20.

1. customquenched with methanol
2. concentrationconcentrated twice from methanol
3. customThe residue was purified through flash column chromatography (CH2Cl2:MeOH, 9:1)
4. concentrationCo-concentration from CH2Cl2 (×2)