Reaction #1340602

Reaction equation

(3S,4S) -1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-propylpyrrolidine

hydrogen

→

title compound

(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-propylpyrrolidine

Solvents

ethanol

Conditions

Workup

1. 1
   OtherInsoluble matter was removed through filtration by use of Celite
2. 2
   Otherethanol was removed under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in diethyl ether (200 mL)
4. 4
   Washthe solution was washed by a 1 mol/L aqueous sodium hydroxide solution (100 mL)
5. 5
   Dryingby drying over anhydrous sodium sulfate
6. 6
   FiltrationAfter filtration
7. 7
   Concentrationthe filtrate was concentrated under reduced pressure

Procedure

A mixture of (3S,4S) -1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-propylpyrrolidine (4.02 g, 11.09 mmol) and a 10% palladium carbon catalyst (1.0 g) in ethanol (100 mL) was stirred hard for 20 hours under an ordinary pressure in a hydrogen atmosphere. Insoluble matter was removed through filtration by use of Celite, and then ethanol was removed under reduced pressure. The residue was dissolved in diethyl ether (200 mL), and the solution was washed by a 1 mol/L aqueous sodium hydroxide solution (100 mL), followed by drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (2.34 g, 92.4%).

Source