Sodium borohydride → HCID 178448421, compound

Participants

Reaction Steps

To a solution of Example 10 (50 mg, 0.13 mmol) in tetrahydrofuran (5 mL) was added sodium borohydride (5.8 mg, 0.15 mmol, Aldrich). The reaction mixture was stirred at room temperature for 6 h and then quenched with saturated aqueous NH4Cl solution. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-5% methanol in methylene chloride) to afford 20 mg (40%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.3 Hz, 3H), 1.24-1.45 (m, 2H), 1.59-1.77 (m, 2H), 3.72 (dd, J=11.7, 4.2 Hz, 1H), 3.80 (s, 3H), 3.84-3.93 (m, 1H), 3.99-4.10 (m, J=7.1 Hz, 2H), 4.56 (d, J=5.2 Hz, 1H), 4.58-4.84 (m, 2H), 5.70 (d, J=5.9 Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 7.44-7.50 (m, 1H), 7.75 (d, J=2.8 Hz, 1H); MS (ESI+) m/z 397 (M+H)+.

Provenance & Evidence