1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2'-fluoro-2-(5-methyl-2-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 200 mL round bottom flask was charged with 66.56E (mixture of diastereomers) (0.59 g, 1.4 mmol), toluene (10 mL), and DBU (2.0 mL, 14 mmol). The resulting solution was stirred for 16 hours at 95° C., cooled to room temperature, and quenched with 1 N HCl. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The initial product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 66.56F (mixture of diastereomers) (0.31 g, 67% yield) as a colorless oil.

Provenance & Evidence