Tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenylethynyl]-pyrrolidine-1-carboxylate → Tert-butyl 2-{2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenyl]-ethyl}-pyrrolidine-1-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenylethynyl]-pyrrolidine-1-carboxylate (Intermediate 38, 3.71 g) in ethanol (100 mL) was treated with 10% palladium on carbon (0.50 g) and stirred under an atmosphere of hydrogen for 4 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give tert-butyl 2-{2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenyl]-ethyl}-pyrrolidine-1-carboxylate (3.21 g) as a colourless gum.

Provenance & Evidence