Triethylamine → HCID 54546551, compound

Participants

Reaction Steps

To a solution of tricyclo[3.3.1.13,7 ]dec-2-yl carbonchloridate [5.77 g, 0.026 mmol, prepared from 2-adamantanol and his (trichloromethyl)carbonate (Horwell, D. C., et al, J. Med. Chem. 1991, 34,404-414)] in 60 mL THF, a solution of DL-α-methyltyrosine methyl ester (5.0 g, 0.0238 mol, prepared from the DL-α-methyltyrosine methyl ester hydrochloride using 1M K2CO3 and EtOAc) in 320 mL THF was added dropwise via an addition funnel, keeping the temperature below 25° C. A solution of triethylamine (4.81 g, 0.047 mol) in 120mL THF was then added dropwise and the heterogeneous reaction mixture was stirred for 16 hours at room temperature under a nitrogen atmosphere. The amine salt was filtered and the filtrate was concentrated in vacuo to givea tan, fluffy solid. Purification by flash chromatography (silica gel, 10% EtOAc/hexane) yielded the title compound. MS: 388 (MH+); 387 (M+).

Provenance & Evidence