Citric Acid → 5H-Pyrrolizine, 6,7-dihydro-1-formyl

HRID 1381100Notes

Reaction equation

HRID 1381100 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][N:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2)#N.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:24]>C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH:4]=[CH:5][N:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2)=[O:24]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 12461845HCID 12461845, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2140555H-Pyrrolizine, 6,7-dihydro-1-formylYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-20 °C

Procedure

13.21 g (0.1 mol) of 7-cyano-2,3-dihydro-1H-pyrrolizine is dissolved in 150 ml of absolute toluene and cooled to -20° C. To this solution is added dropwise 108 ml (0.13 mol) of a 1.2-molar diisobutyl aluminum hydride solution in toluene; the mixture is then warmed to room temperature, stirred for another hour, and decomposed with 300 ml of 10% aqueous citric acid solution. The product is extracted with methylene chloride, the organic phase is dried, concentrated, and the residue recrystallized from ether, thus obtaining 8.0 g (59% of theory) of 7-formyl-2,3-dihydro-1H-pyrrolizine, mp 58° C.

Workup

  1. temperaturethe mixture is then warmed to room temperature
  2. extractionThe product is extracted with methylene chloride
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customthe residue recrystallized from ether

Sources & evidence

ORD record
ord-c3bacd9303494e008bd61fbe24141dc0
Source dataset
uspto-grants-1986_04
Patent number
US04585771

Reaction notes

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