Water → HCID 66821897, compound

Participants

Reaction Steps

To a solution of Example 20 (60 mg, 0.12 mmol) in EtOH/CHCl3 (1:1; 1.2 mL) was added portionwise NaBH4 (9.6 mg, 0.25 mmol). After 10 minutes of stirring, water (1 mL) was added and the reaction mixture was concentrated in vacuo. The residue was partitioned between DCM and water. The organic layer was washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and concentrated in vacuo. The resulting gum was freeze-dried to give the title compound (30 mg, 60%) as an off-white solid. δH (CDCl3) 8.28 (1H, s), 7.96 (1H, d, J=2.14 Hz), 7.90 (1H, s), 7.65 (1H, dd, J 7.56, 1.39 Hz), 7.52 (1H, dd, J 7.97, 1.41 Hz), 7.12 (1H, t, J=7.76 Hz), 6.59 (1H, br d, J=9.42 Hz), 6.48-6.46 (2H, m), 5.75-5.66 (1H, m), 3.94-3.85 (1H, m), 3.83-3.74 (1H, m), 3.65-3.51 (2H, m), 3.18 (3H, s), 1.86 (3H, d, J=6.80 Hz). LCMS (ES+) 398 (M+H)+, RT 19.67 minutes (Method 6).

Provenance & Evidence