Sodium borohydride → HCID 178495824, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of Example 127 (47.0 mg, 0.14 mmol) in methanol (3 mL) was added a solution of sodium borohydride (6.0 mg, 0.15 mmol) in methanol (3 mL). The reaction mixture was stirred at 0° C. for 30 minutes and then warmed to reflux for 1 hour. The reaction mixture was then cooled, quenched with aqueous 1 M aqueous HCl, neutralized with saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.48-1.65 (m, 4H), 1.66-1.82 (m, 4H), 2.08 (s, 1H), 2.12 (s, 1H), 2.23 (s, 3H), 2.26 (s, 2H), 2.52-2.59 (m, 1H), 3.24 (s, 3H), 3.66 (t, J=5.6 Hz, 2H), 4.34 (t, J=5.8 Hz, 2H), 4.46 (d, J=4.4 Hz, 2H), 5.29 (t, 1H); MS (ESI+) m/z 351 (M+H)+.

Provenance & Evidence