Triethylamine → (1R*,2R*,4'S*,5S*,6R*)-8-Benzyl-4'-(2-benzyloxy-5-trifluoromethoxyphenyl)-2',3',4',5'-tetrahydro-1-phenyl-6-phenylsulfonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Participants

Reaction Conditions

Reaction Steps

Palladium acetate (140 mg, 0.6 mmol) was added to a degassed suspension of (1R*,2R*,5S*,6R*)-8-benzyl-2′,5′-dihydro-1-phenyl-6-phenylsulfonylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan] (Description 15; 2.9 g, 6.15 mmol), 2-benzyloxy-5-trifluoromethoxyiodobenzene (7.3 g, 18.5 mmol), tetrabutylammonium chloride, (1.7 g, 6.15 mmol), lithium chloride (2.6 g, 62 mmol), triethylamine (2.6 ml, 18 mmol), potassium formate (1.56 g, 18.5 mmol), N,N-dimethylformamide (40 ml) and water (3 ml). The mixture was stirred at 60° C. for 72 hours then partitioned between brine and ethyl acetate. The organic layer was washed (×3) with water then dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5, 10, 15 and 30% ethyl acetate/iso-hexanes to yield the title compound (2.0 g, 44%).

Provenance & Evidence