Triethylamine → HCID 60152317, compound

Participants

Reaction Steps

Stir a mixture of 3-dimethylaminomethyl-2-(3-fluoro-5-hydroxy-phenyl)-bicyclo[4.1.0]heptan-2-ol (295 mg, 1.06 mmol), 2,2-dimethyl-propionyl chloride (153 mg, 1.27 mmol) and triethyl-amine (321 mg, 3.18 mmol) in CH2Cl2 (40 mL) at ambient temperature for 5 hours. Quench the mixture with 10 mL of H2O, Separate the aqueous layer off, and concentrate the organic layer under reduced pressure. Purify the residue by preparative TLC to give 2,2-dimethyl-propionic acid 3-(3-dimethylaminomethyl-2-hydroxy-bicyclo[4.1.0]hept-2-yl)-5-fluoro-phenyl ester as white solid (228 mg, Yield: 59.2%). MS (m/z): 364 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.25-7.28 (d, J1=10.4, J2=1.6, 1H), 7.14 (s, 1H), 6.76-6.78 (d, J1=9.2, J2=2.4, 1H), 2.37-2.46 (m, 1H), 2.15-2.19 (m, 7H), 1.99-2.03 (d, J=13.2, 1H), 1.82 (m, 2H), 1.53-1.68 (m, 2H), 1.37 (s, 9H), 1.17 (m, 1H), 1.01-1.06 (m, 1H), 0.75-0.81 (m, 1H), 0.48-0.50 (m, 1H).

Provenance & Evidence