Sodium Carbonate → (rac.)-(1R*,5S*)-3-(4-Hydroxy-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene-2,8-dicarboxylic Acid 8-tert-butyl Ester 2-methyl Ester

Participants

Reaction Conditions

Reaction Steps

Aq. 2M Na2CO3 (90.0 mL) was added to a mixture of compound A1 (10.1 g, 24.4 mmol) and 4-hydroxybenzeneboronic acid (3.37 g, 24.4 mmol) in DME (180 mL). The mixture was degassed with N2 for 3 min, and Pd(PPh3)4 (1.42 g, 1.23 mmol) was added. The mixture was heated quickly to 80° C., and stirred at this temperature for 1 h. The mixture was allowed to cool to rt, and was partitioned between EtOAc (250 mL) and water (250 mL). The org. phase was washed with water. The combined aq. layers were extracted with EtOAc. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:1) yielded the title compound (7.27 g, 83%). LC-MS: tR=0.94 min; ES+: 360.29.

Provenance & Evidence