Tributylstannane → (1R*,2R*,5S*,6R*)-8-Benzyl-2',5'-dihydro-1-phenyl-6-phenylsulfonyl-4'-tributylstannylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.26 mmol) was added to a degassed solution of (1R*,2R*,5S*,6R*)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol (Description 13; 1.8 g, 3.7 mmol) in tetrahydrofuran (50 ml). The mixture was cooled to +5° C. before tri-n-butyltin hydride (1.3 g, 4.4 mmol) was added. The mixture was allowed to warm to room temperature and stirred for a further 18 hours before triphenylphosphine (1 g, 3.7 mmol) and diethyl azodicarboxylate (0.65 g, 3.7 mmol) were added. After 3 hours the mixture was concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5 and 10% ethyl acetate/iso-hexanes to give the title compound (154 mg, 5.5%).

Provenance & Evidence