(1R*,2R*,5S*,6R*)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol → (1R*,2R*,5S*,6R*)-8-Benzyl-2-[(Z)-3-hydroxypropenyl]-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

Participants

Reaction Steps

Lindlar catalyst (200 mg) was added to a 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; 2.1 g, 4.3 mmol) in ethyl acetate (100 ml). The mixture was stirred at room temperature for 8 hours then filtered through Celite™ and the filtrate concentrated in vacuo to yield the title compound (1.88 g, 90%).

Provenance & Evidence