反应详情

A mixture of methyl 3-(4-acetamidophenylsulfonyl)propionate (54.2 g, 190 mmol), sodium borohydride (22.3 g, 590 mmol), and 400 mL of t-butanol was stirred mechanically and heated to reflux. Methanol (11 mL) was added dropwise over 20 minutes, and the resulting solution was stirred at reflux for 2 hours. The reaction mixture was cooled, and 250 mL of 3M aqueous HCl was added slowly with vigorous gas evolution occurring. The resulting mixture was partially concentrated at reduced pressure to remove t-butanol, and the residue was heated at reflux for 2 hours. The mixture was cooled, and solid sodium bicarbonate was added slowly until the pH of the mixture was 6-7. The mixture was allowed to stand several hours at 23° C. and then the precipitated product was filtered. After recrystallization from methanol containing a small amount of ether, 8.2 g (20%) of cream-colored powder was obtained, mp 99°-102° C.

1. temperatureheated to reflux
2. stirringthe resulting solution was stirred
3. temperatureat reflux for 2 hours
4. temperatureThe reaction mixture was cooled
5. concentrationThe resulting mixture was partially concentrated at reduced pressure
6. customto remove t-butanol
7. temperaturethe residue was heated
8. temperatureat reflux for 2 hours
9. temperatureThe mixture was cooled
10. additionsolid sodium bicarbonate was added slowly until the pH of the mixture
11. waitto stand several hours at 23° C.
12. filtrationthe precipitated product was filtered
13. customAfter recrystallization from methanol containing a small amount of ether