Sodium borohydride → HCID 71522897, compound

Participants

Reaction Steps

To a solution of Example 265D (140 mg, 0.43 mmol) in THF (4 mL) and MeOH (4 mL) was added NaBH4 (60 mg, 2.5 mmol) and the solution was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4Cl solution and the resulting mixture extracted with EtOAc (10 mL×3). The combined organic phases were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by Prep-HPLC to obtain the title compound (0.11 g, 76% yield) as a white solid. MS: m/z 333 (M+H); 1H NMR: (400 MHz, CDCl3): δ 8.57 (d, J=4.3 Hz, 1H), 7.67 (t, J=6.8 Hz, 1H), 7.31-7.23 (m, 2H), 4.73 (s, 1H), 4.55-4.43 (m, 1H), 3.56-3.26 (m, 2H), 3.13-2.79 (m, 2H), 2.28-2.07 (m, 3H), 2.05-1.85 (m, 2H), 1.75-1.70 (m, 4H), 1.46 (s, 9H).

Provenance & Evidence