Stannane, tributyl(1-ethoxyethenyl)- → (3aR,6aS)-tert-Butyl 5-(5-(1-ethoxyvinyl)pyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

The product from Example 64A (107 mg, 0.29 mmol) and tributyl-(1-ethoxyvinyl)stannane (157 mg, 0.43 mmol) were combined in a 100 mL conical flask with toluene (4 mL). Tetrakis(triphenylphosphine)palladium(0) (19.7 mg, 0.017 mmol) was added, and the mixture was heated under nitrogen at 90° C. for 22 h. The black mixture was cooled to room temperature, applied to a column of silica gel and eluted with hexanes-EtOAc (1:1) to provide the titled compound as an amber gum (contaminated with triphenyl phosphine oxide, 47 mg, 47% pure, 21% yield). MS(DCI/NH3) m/z 360 (M+H)+.

Provenance & Evidence