Toluene → HCID 68211704, compound

Participants

Reaction Conditions

Reaction Steps

(2S,3′S)-2-Methyl-[1,3′]bipyrrolidinyl dihydrochloride (1.1 g, 4 mmol) was treated with NaOt-Bu (1.1 g, 2equiv) in MeOH (30 mL), filtered, and concentrated. To this flask was charged with tert-Butyl-4-bromo-benzoate (1 g, 3.89 mmol), sodium tert-butoxide 538 mg, 5.6 mmol), tris(dibenzylideneacetone)dipalladium-(0) (35 mg, 0.039 mmol), BINAP (72 mg, 0.116 mmol), and toluene (40 mL) under argon. The reaction flask was heated to 80° C. (external) for 24 h with stirring until the starting material had been completely consumed as judged by TLC analysis. The mixture was allowed to cool to room temperature, taken up in DCM (50 mL), filtered, and concentrated. The crude product was then purified further by flash chromatography on a silica gel column eluted with 0-5% of 7N NH3/MeOH in DCM to get 1.02 g (80%) of the title compound as a yellow oil.

Provenance & Evidence