反应详情

A mixture of (3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-ol (P0016; 445 mg) and 4-chlorobenzaldehyde (192 mg) in toluene (15 ml) was refluxed for 2 hours. And then to the resulting mixture of the Schiffs base was added manganese triacetate (733 mg) and the reaction mixture was refluxed for 1 hour. The precipitated manganese diacetate was then separated by filtration and the solvent was removed under reduced pressure. The crude product was purified by silica gel (26 g) column chromatography eluting with hexane/ethyl acetate (20:1) to give (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]pentan-3-ol (P0012; 465 mg).

1. temperaturewas refluxed for 2 hours
2. additionAnd then to the resulting mixture of the Schiffs base
3. temperaturethe reaction mixture was refluxed for 1 hour
4. customThe precipitated manganese diacetate was then separated by filtration
5. customthe solvent was removed under reduced pressure
6. customThe crude product was purified by silica gel (26 g) column chromatography
7. washeluting with hexane/ethyl acetate (20:1)