Triethylamine → Benzaldehyde

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Reaction Steps

Trifluoromethanesulfonic anhydride (9.7 mL) is added to a solution of 3-benzyl-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-ol (13.7 g, the compound may be obtained by reductive amination of benzaldehyde with (2R,6S)-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-ol and NaHB(OAc)3 in 1,2-dichloroethane), triethylamine (43 mL), and 4-dimethylaminopyridine (50 mg) in dichloromethane (135 mL) chilled to −10° C. under argon atmosphere. The solution is stirred at ca. −5° C. for 30 min and then at room temperature overnight. The solution is added to ice-cold water and then aqueous ammonia solution is added. The resulting mixture is extracted with dichloromethane, the combined organic extracts are washed with water and dried (MgSO4). The solvent is removed under reduced pressure to give the crude product that is used without further purification.

Provenance & Evidence