反应详情

1-(4-Benzyloxyphenyl)propan-2-one (2.28 g) was added to a solution of 2-hydroxy-2-(3-chlorophenyl)ethanamine (1.75 g) in dry toluene (100 ml) and the solution was boiled under reflux for 90 minutes in an apparatus incorporating a water-trap. The solution was cooled and the solvent removed under reduced pressure. The residue, dissolved in methanol (100 ml), was cooled to less than 10° C. and treated portionwise with sodium borohydride (3.0 g) over 30 minutes, with stirring. The mixture was stirred for one hour at room temperature and the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried (magnesium sulphate), filtered and evaporated to dryness to give a solid. Trituration of the solid with diethyl ether followed by addition of hexane and filtration gave N-[2-(4-benzyloxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine of analytical purity, mp 95°-99° C., as a 45:55 mixture of diastereoisomers.

1. temperatureunder reflux for 90 minutes in an apparatus
2. temperatureThe solution was cooled
3. customthe solvent removed under reduced pressure
4. dissolutionThe residue, dissolved in methanol (100 ml)
5. temperaturewas cooled to less than 10° C.
6. additiontreated portionwise with sodium borohydride (3.0 g) over 30 minutes
7. stirringThe mixture was stirred for one hour at room temperature
8. customthe solvent removed under reduced pressure
9. dissolutionThe residue was dissolved in ethyl acetate
10. washwashed with water
11. dry with materialdried (magnesium sulphate)
12. filtrationfiltered
13. customevaporated to dryness
14. customto give a solid