Triethylamine → HCID 11265900, compound

Participants

Reaction Steps

To the suspension of (2S,3S)-2,3-dibenzylsuccinic anhydride thus obtained in anhydrous toluene (3.5 mL) were added triethylamine (361 mg, 2.54 mmol) and trimethylsilyltrifluoromethanesulfonic acid (565 mg, 2.54 mmol) with stirring under ice cooling, and the mixture was stirred at 90° C. for 2 h. To the reaction mixture with stirring under ice cooling was added dropwise a solution of tetrabutylammonium bromide (2.7 mg, 0.00845 mmol) in dichloromethane (3 mL) and bromine (140 mg, 0.876 mmol), and the reaction mixture was stirred at the same temperature for 30 min. The reaction mixture was directly concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 8:1) to give 59 mg of the title compound as a solid (2 step yield: 25%).

Provenance & Evidence