Sodium borohydride → HCID 16005234, compound

Participants

Reaction Conditions

Reaction Steps

2-(2′-Formylbiphenyl-4-yl)-N-isobutyl-2-methylpropanamide (example 37) (190 mg, 0.59 mmol) was dissolved in anhydrous MeOH (6 mL) and the mixture was cooled to 0° C. A solution of NaBH4 (45 mg, 1.2 mmol) in anhydrous MeOH (4 mL) was then added to the solution. The mixture was stirred for 4 hrs at room temperature and then evaporated. The residue was dissolved in EtOAc and washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was successively purified on preparative RP HPLC (acetonitrile/water) and on silica gel (EtOAc/hexanes) and co-evaporated with ethanol to give 119 mg (62%) of white crystals. 1H NMR (400 MHz, dMSO): δ 0.72-0.74 (d, 6H), 1.47 (s, 6H), 1.67-1.70 (m, 1H), 2.82-2.86 (t, 2H), 4.37-4.38 (d, 2H), 5.01-5.1 (t, 1H), 7.17 (d, 1H), 7.27-7.36 (m, 7H), 7.53-7.55 (d, 1H); MS+H (326).

Provenance & Evidence