Diisopropylcarbodiimide → HCID 59536414, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.05 g, 0.2 mmol) in DMF (1 mL) was treated with N-((isopropylimino)methyl-ene)propan-2-amine (0.07 mL, 0.5 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (0.04 g, 0.2 mmol), and 1-adamantanecarboxylic acid (TCI, 0.04 g, 0.2 mmol). The resulting mixture was heated at 65° C. for 12 h. The reaction was cooled to RT and the filtrate was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give the pure product. It was dissolved in methanol (10 mL) and neutralized by passing the solution through a Polymer Lab-HCO3 Macroporous resin cartridge, and the filtrate was concentrated to give (1R)-2-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylcarbonyl)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline as a colorless solid. MS (ESI, positive ion) m/z: 440 (M+H).

Provenance & Evidence