Sodium Bicarbonate → HCID 22722137, compound

Participants

Reaction Steps

3-(4-Chlorophenyl)-3-(5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocin-3-yl)cyclobutanone (4-5) (52 mg) was dissolved in freshly distilled tetrahydrofuran (2 mL). Methyltriphenylphosphonium bromide (281 mg) was added followed by potassium bis(trimethylsilyl)amide (KHMDS, 0.5M in toluene, 1.25 mL). After stirring for 24 hours at room temperature, the crude product was added to a saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated. The product was purified by silica gel column chromatography to give 3-[1-(4-chlorophenyl)-3-methylenecyclobutyl]-5,6,7,8,9, 10-hexahydro[1,2,4]triazolo[4,3-a]azocine (4-6).

Provenance & Evidence