Potassium bisulfate → HCID 17917748, compound

Participants

Reaction Conditions

Reaction Steps

The amide from above (4.7 g, 14.7 mmol) was dissolved in 50 mL THF and added to a slurry of LiAlH4 (558 mg, 14.7 mmol) in 50 mL THF at −78° C. The reaction mixture was allowed to warm to 0° C. and maintained for 15 min, after which time it was cooled to −78° C. and cannulated into an ice-cooled solution of KHSO4 (8.16 g, 60 mmol) in 200 mL H2O. The resulting mixture was extracted with 5×100 mL EtOAc. The combined extracts were washed with 2×100 mL satd.NaHCO3 and 1×100 mL brine, dried with Na2SO4 and evaporated to an oily residue which was flash chromatographed through SiO2 (25% EtOAc/hexane—35% EtOAc/hexane) yielding 2.8 g (86%) of pyridine-2-carboxylic acid (1-formyl-3-methylbutyl)amide as a colorless oil which solidified on standing.

Provenance & Evidence