Reaction #1987

Reaction equation

Ammonium chloride

compound

N-benzyl-3,4-pyrrolidinedicarboxylic acid diethyl ester

THF

NH3

→

title compound

2-benzyl-4,6-dioxooctahydropyrrolo[3.4-c]pyridine

Conditions

Workup

1. 1
   workup.ADDITIONwas added over a 10 minute period
2. 2
   workup.STIRRINGthe reaction mixture was stirred at -33° C. for 3 hours
3. 3
   workup.STIRRINGwith stirring
4. 4
   Temperaturethe mixture was warmed to room temperature
5. 5
   Otherthe excess ammonia was evaporated
6. 6
   workup.ADDITIONTo this was added 60 mL of water
7. 7
   Extractionthe mixture was extracted with methylene chloride
8. 8
   WashThe extract was washed with brine
9. 9
   Otherdried
10. 10
    Concentrationconcentrated
11. 11
    OtherThe residue was chromatographed on silica gel

Procedure

A solution of 9.00 mmol of Na in liquid NH3 was prepared at -78° C. To this was added 15 mg of FeCl3, and the reaction mixture was warmed to -40° C. To this solution, stirred under N2, a cooled (-40° C.) solution of the compound (957 mg) from step 457a in THF was added over a 10 minute period, and the reaction mixture was stirred at -33° C. for 3 hours. Ammonium chloride (1.5 g) was added with stirring, then the mixture was warmed to room temperature and the excess ammonia was evaporated. To this was added 60 mL of water, and the mixture was extracted with methylene chloride. The extract was washed with brine, dried and concentrated. The residue was chromatographed on silica gel to give 425 mg of the title compound.

Source