Aluminium lithium hydride → HCID 23452592, compound

HRID 1278062Notes

Reaction equation

HRID 1278062 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([CH:14]2[CH2:16][CH2:15]2)=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[CH2:12][CH:14]2[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23452508HCID 23452508, compound

Product 1

HCID 23452592HCID 23452592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 3.0 g of 2-(4-chlorobenzyl)-1-cyclopropylcarbonylpyrrolidine in 30 ml of tetrahydrofuran, and add the thus-prepared solution (dropwise, within 10 minutes at 0°, with stirring) to a suspension of 0.43 g of lithium aluminum hydride (=lithium hydrido-aluminate) in 10 ml of tetrahydrofuran. Subsequently, boil the resulting reaction mixture under reflux for 1 hour. After cooling, cautiously add 50 ml of water thereto and extract the product 3 times with, in each case, 30 ml of diethyl ether. Combine the ether solutions and wash the combined extract with saturated sodium chloride solution. Dry the washed ether phase over sodium sulfate, evaporate off the solvent and distil the residue twice under a vacuum to obtain 1.65 g (58% of theory) of the title compound (b.p. 108° at 0.006 mm of Hg).

Workup

  1. additionadd the thus-prepared solution (dropwise, within 10 minutes at 0°
  2. customthe resulting reaction mixture
  3. temperatureunder reflux for 1 hour
  4. temperatureAfter cooling
  5. extractioncautiously add 50 ml of water thereto and extract the product 3 times with, in each case, 30 ml of diethyl ether
  6. washwash the
  7. extractioncombined extract with saturated sodium chloride solution
  8. dry with materialDry the washed ether phase over sodium sulfate
  9. customevaporate off the solvent
  10. customdistil the residue twice under a vacuum

Sources & evidence

ORD record
ord-88b79d73c664480aa59312c9419a81fa
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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