Acetic Acid → HCID 53749786, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the crude aldehyde 20-8 (0.671 g,.1.88 mmol), amine 15-8 (0.651 g, 2.44 mmol), acetic acid (0.107 mL, 1.88 mmol), NaOAc (1.54 g, 18.8 mmol), and powdered molecular sieves (1.20 g) in 2-propanol (15 mL) was stirred for 20 minutes. The mixture was cooled to 0° C. and then NaBH3CN (0.354 g, 5.64 mmol) was added. After stirring 6 hours, the pH of the mixture was adjusted to ~2 with 1N HCl. The solution was stirred for an additional 10 minutes, ethyl acetate (20 mL) was added, and the pH was adjusted to ~11 with 10% potassium carbonate. The organics were extracted with ethyl acetate, dried over Na2SO4, and removed in vacuo. The residue was chromatographed (silica gel, [70:25:5 CHCl3 /EtOAc/MeOH]) to give 20-9 as a yellow oil in 95% yield.

Provenance & Evidence