HCID 21931792, compound → HCID 21931744, compound

Participants

Reaction Steps

To 3,3-Dimethoxy-2,3,4,5-tetrahydro-1H-[2,3′]bipyridinyl-6-one (1.0 g, 421 mmol) in 3 mL THF was added borane-dimethylsulfide complex (3.0 mL, 6.0 mmol of a 2 M solution in THF) at 0° C. The solution was stirred at rt overnight, and was then quenched with methanol and heated at reflux for 2 h. The methanol was removed under vacuum and the residue was partitioned between water and chloroform. The mixture was acidified to pH=3 and washed with CHCl3 (3–10 mL). The aqueous material was then basifed to pH=8 with solid NaHCO3 and then was extracted with CHCl3 (3×15 mL). The extracts were dried over MgSO4 and concentrated to give 812 mg (86%) of a pale yellow oil: mass spectrum m/e=223.

Provenance & Evidence