Triethylamine → 4-[1-(4'-tert-Butyl-biphenyl-4-ylamino)-3-methyl-butyl]-benzoic acid methyl ester

Participants

Reaction Steps

To a solution of 4-(3-methyl-butyryl)-benzoic acid methyl ester (Preparation 4) (440 mg, 2 mmol) in dichloromethane (30 mL) is added 4′-tert-butyl-biphenyl-4-ylamine (Preparation 1) (450 mg, 2 mmol), and triethylamine (606 mg, 6 mmol). Titanium(IV) chloride in dichloromethane (1M, 1 mL) is added dropwise. The reaction is monitored by TLC. Once the starting material is consumed, the reaction is carefully quenched with sodium cyanoborohydride (377 mg, 6 mmol) in MeOH (5 mL) and stirred for 2 h. The reaction is adjusted to pH=13 with 5N NaOH, extracted with EtOAc, dried (Na2SO4), and concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography, eluting with dichloromethane to afford 718 mg of the titled compound. 1H-NMR.

Provenance & Evidence