Phosphoric Acid → Dicyclohexylamine

Participants

Reaction Steps

Seventy mg of molecular sieves 4A was added to a stirred mixture of 62 mg of orthophosphoric acid, 52 μL of tri-n-butylamine and 0.7 mL of acetonitrile at room temperature, and the mixture was stirred in an ice-bath. To the mixture was added 70 mg of 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-D-erythropentofuranosyl chloride, and the mixture was reacted at the same temperature for 1 day. Then, to the mixture were added 156 μL of tri-n-butylamine and then deionized water. The mixture was extracted with toluene three times. To the organic layer was added 48 μL of cyclohexylamine and the mixture was stirred for 30 min. The mixture was concentrated in vacuo, and acetone was added to form a precipitate, which was collected by filtration. The residue was washed with chloroform and dried in vacuo at room temperature to give a dicyclohexylamine of compound (29) as a white solid.

Provenance & Evidence