Hydrochloric Acid → HCID 69342993, compound

Participants

Reaction Steps

A solution of 440 mg of 4-(1,1-dimethyl-butyl)-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (1.17 mmol) in 10 ml of THF was added dropwise to 4.66 ml of a 1 molar solution of BH3-THF complex in THF at 0° C. The reaction mixture was stirred for 1 h at rt and then heated to reflux overnight. Upon cooling to rt 2 ml of 6N HCl were added and the mixture was stirred for 1 h. Then the pH was adjusted to 9 by addition of 1 N sodium hydroxide solution and the mixture was extracted three times with EtOAc. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. This gave 422 mg (100%) of [4-(1,1-dimethyl-butyl)-benzyl]-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine as a light yellow oil which was used in the following coupling step without further purification. MS (ISP) 364.2 (M+H)+.

Provenance & Evidence