Potassium Carbonate → (1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(1-methoxycarbonylmethyl-1H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane

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Reaction Steps

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-6-(tetrazol-5-yl)-8-azabicyclo[3.2.1]octane (Example 138; 2 g, 3.4 mmol), methyl bromoacetate (0.5 ml, 5.1 mmol) and potassium carbonate (0.75 g, 0.51 mmol) were stirred in acetonitrile (20 ml) at 45° C. for 90 minutes. After this time the mixture was concentrated in vacuo and the residue partitioned between brine and ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated. The residual clear oil was chromatographed on silica gel eluting with 10, 20 and 50% ethyl acetate/iso-hexanes to yield the title compounds: isomer A (1.2 g, 54%) and isomer B (0.9 g, 40%).

Provenance & Evidence