2-Amino-1-[3-(trifluoromethyl)phenyl]ethan-1-ol → N-[2-(4-Methylphenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

Participants

Reaction Steps

A mixture of 2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (2.05 g) and 4-methylphenylacetone (1.48 g) was refluxed in benzene (70 ml) under Dean & Stark conditions for 4h. The solvent was removed under reduced pressure, replaced with methanol and sodium borohydride (3 g) added portionwise. The solvent was evaporated under reduced pressure, the residue partitioned between water and ether and the ether layer dried (MgSO4). Removal of the solvent under reduced pressure gave an oil which was dissolved in methanol and treated with an equivalent amount of methanolic fumaric acid. Evaporation of the solvent gave the title compound (fumarate salt) as a 58:42 mixture of diastereoisomers, mp 138°-144° (EtOAc).

Provenance & Evidence