Benzoic Acid → HCID 58375026, compound

Participants

Reaction Steps

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (155 mg; alternatively, N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate may be used) is added to a solution of benzoic acid (60 mg) and ethyldiisopropylamine (0.25 mL) in dichloromethane (1 mL; DMF may be used as well). The resulting solution is stirred at ambient temperature for 15 min before it is cooled in an ice bath. (2R,6S)-6,11,11-Trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-ol (0.10 g) is added and the solution is warmed to room temperature and stirred overnight. The mixture is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (H2O/MeCN) to give the product as a beige solid.

Provenance & Evidence