Tris(propan-2-yl)silanethiol → 4-(2-Triisopropylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Bis[(2-diphenylphosphino)phenyl]ether (0.43 g; 0.80 mmol) and tris(dibenzylideneacetone)-dipalladium (0.37 mg; 0.40 mmol) were dissolved in 40 mL toluene. 4-[2-(Nonafluorobutane-1-sulfonyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (4.34 g; 7.76 mmol), triisopropyl-silanethiol (1.83 mL; 8.53 mmol) and sodium tert-butoxide (0.90 g; 9.3 mmol) were added and the reaction mixture was stirred under argon for 3 hours at 100° C. The reaction mixture was cooled to room temperature filtered through a pad of silica and concentrated in vacuo. The residue was purified by flash chromatography (silica gel; ethyl acetate/heptane) to give 1.58 g 4-(2-triisopropylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (3.51 mmol; 45%).

Provenance & Evidence