Methanol → HCID 58938541, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-((dipropylamino)methyl)-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate (0.228 g, 0.51 mmol) was dissolved in tetrahydrofuran (3.5 mL). The solution was cooled to −40° C. and diisobutylaluminum hydride (DIBAL-H) (1M, 1.5 mL, 1.5 mmol) was added rapidly. The reaction stirred for 1 h and was warmed to room temperature. Methanol and Rochelle's salt were added and the mixture stirred at room temperature for 3 h. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried, concentrated, and flash chromatographed (2% methanol/ethyl acetate) to give 0.096 g (46% yield) of the desired product.

Provenance & Evidence