Diisobutylaluminum hydride → HCID 59232219, compound

Participants

Reaction Steps

To a stirred solution of Example 234 (150 mg, 0.30 mmol) in THF (2 mL) at 0° C., was added DIBAL-H (2.96 mL, 2.96 mmol, 1.0 M in THF). The reaction was allowed to stir for 30 min while warming to rt. The mixture was quenched with MeOH (1 mL) and diluted with EtOAc (300 mL) and saturated aq sodium potassium tartrate (200 mL). This solution was stirred at 50° C. for 17 hr. The mixture was allowed to cool and the organic phase was washed with brine (50 mL), dried (Na2SO4) and concentrated to dryness. The residue was purified by preparative HPLC using a gradient elution from 10% to 70% acetonitrile to obtain 31 mg (20%) of the desired product. 1H-NMR (DMSO-d6) δ 9.51 (br s, 1H), 9.35 (br s, 1H), 8.73 (d, J=6.0 Hz, 1H), 8.35 (t, J=8.7 Hz, 1H), 7.98 (s, 1H), 7.62-7.55 (m, 1H), 7.49-7.47 (m, 1H), 7.41-7.27 (m, 2H), 6.76 (s, 1H), 5.27 (t, J=5.7 Hz, 1H), 4.59-4.58 (m, 1H), 4.11 (s, 1H), 3.39 (d, J=6.9 Hz, 2H); MS [M+H]+=509.2; LCMS RT=2.98 min.

Provenance & Evidence