Triethylamine → 4'-({2-[(4,4-Dimethylcyclohexyl)amino]ethyl}oxy)-2'-methyl-3-biphenylcarboxamide trifluoroacetate

Participants

Reaction Steps

To a solution of 4′-[(2-aminoethyl)oxy]-2′-methyl-3-biphenylcarboxamide trifluoroacetate (0.105 g; 0.273 mmol; Intermediate VII-1) and 4,4-dimethylcyclohexanone (0.038 g; 0.30 mmol; Intermediate Step 1 of III-1) in MeOH/CH2Cl2/HOAc (3 mL; 1:1 MeOH/CH2Cl2 with 5% HOAc) was added Et3N (0.040 mL; 0.27 mmol), followed by PS—BH3CN (0.32 g; ca. 4.2 mmol/g; ca. 1.35 mmol BH3CN). The mixture was agitated overnight at rt using an orbital shaker, and the resin was removed by filtration. The filtrate was concentrated in vacuo, and the residue was purified by RP-HPLC (C18 column, MeCN/H2O gradient with TFA additive) affording the title compound as a colorless foam. (LC/MS Method C) 2.24 min, m/z 381 (M+1, freebase).

Provenance & Evidence