Réaction #1340599

Équation de réaction

p-Toluenesulfonyl chloride

(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-hydroxymethylpyrrolidine

ethyl acetate

hydrochloric acid

→

title compound

(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-(p-toluenesulfonyloxy)methylpyrrolidine

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   TempératureUnder cooling
2. 2
   Extractionfollowed by extraction with ethyl acetate (200 mL×2)
3. 3
   LavageThe organic layer was washed sequentially by 1 mol/L hydrochloric acid (100 mL), saturated sodium hydrogencarbonate (100 mL), and saturated brine (100 mL)
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   FiltrationAfter filtration
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   AutreThe residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Mode opératoire

(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-hydroxymethylpyrrolidine (5.00 g, 14.3 mmol) was dissolved in pyridine (50 mL). p-Toluenesulfonyl chloride (4.08 g, 21.4 mmol) and 4-(N,N-dimethyl)aminopyridine (174 mg, 1.43 mmol) were added thereto at room temperature, and the resultant mixture was stirred under a nitrogen atmosphere for 24 hours. Under cooling, ethyl acetate (200 mL) and 1 mol/L hydrochloric acid (200 mL) were added thereto, followed by extraction with ethyl acetate (200 mL×2). The organic layer was washed sequentially by 1 mol/L hydrochloric acid (100 mL), saturated sodium hydrogencarbonate (100 mL), and saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate:n-hexane=1:1), to thereby yield the title compound as a colorless amorphous substance (6.27 g, 87%).

Source