Reaction #2945

ord-fc50405695d1443a80eda06a3dd99d45

Reaction equation

C=C1CC(=O)O1.CC(C)=O
diketene acetone
C1CCNC1
pyrrolidine
→
CC(=O)CC(=O)N1CCCC1
title compound
Yield 97.9%
CC(=O)CC(=O)N1CCCC1
1-(3-Oxobutyryl)pyrrolidine
Yield 97.9%

Reactants

C=C1CC(=O)O1.CC(C)=O
diketene acetone
C1CCNC1
pyrrolidine

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otheras described in preparation 7
  2. 2
    OtherThe solvent was removed in vacuo
  3. 3
    Otherthe residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→1%)

Procedure

9 ml (0.05 mol) of diketene-acetone adduct and a solution of 4.2 ml (0.05 mol) of pyrrolidine in 20 ml of toluene were treated as described in preparation 7. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→1%) yielding 7.6 g of the title compound as a dark oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731322uspto-grants-1998_03