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

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Reaction Steps

Diethylazodicarboxylate, 0.15 g, 0.86 mmol was added to a solution of (1R*,2 R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxyl 1-phenyl-6-(tetrazol-5-yl)-8-azabicyclo[3.2.1]octane (Example 138; 0.5 g, 0.85 mmol), [N-(t-butoxy-carbonyl)ethanolamine] (0.15 g, 0.93 mmol) and triphenylphosphine (0.23 g, 0.88 mmol) in dichloromethane (20 ml). The mixture was stirred at room temperature for 2 hours then concentrated in vacuo. The residue was chromatographed on silica gel eluting with 10, 20 and 30% ethyl acetate/iso-hexanes to yield the title compound (543 mg, 88%).

Provenance & Evidence