Diisobutylaluminum hydride → HCID 15136239, compound

HRID 341772Notes

Reaction equation

HRID 341772 reaction equation
C([O:3][C:4]([C:6]1[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1.CCCCCC>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH:10]=[C:6]([CH2:4][OH:3])[CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 538881261-tert-Butyl 3-ethyl 2,5-dihydro-1H-pyrrole-1,3-dicarboxylate

Product 1

HCID 15136239HCID 15136239, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5.43 g (22.5 mmol) 2,5-dihydro-pyrrole-1,3-dicarboxylic acid 1-tert.-butylester 3-ethyl ester in 50 ml THF, cooled to -78° C. was dropwise added 50 ml of a 1N DIBAL-H solution in hexane. The mixture was allowed to warm to room temperature overnight. As TLC analysis indicated complete consumption of starting material, the mixture was cooled in an ice bath and 1.90 g water were cautiously added, followed by 1.90 g 15% aqueous NaOH and 5.70 g water. The white precipitate was filtered off, washed thoroughly with ether and the combined filtrates were evaporated. Bulb-to-bulb distillation of the residual pale yellow oil gave 4.13 g (93%) 3-hydroxymethyl-2,5-dihydro-pyrrole-1-carboxylic acid tert.-butylester as a colorless oil, b.p. 130° C. (0.2 mbar).

Workup

  1. customconsumption of starting material
  2. temperaturethe mixture was cooled in an ice bath
  3. addition1.90 g water were cautiously added
  4. filtrationThe white precipitate was filtered off
  5. washwashed thoroughly with ether
  6. customthe combined filtrates were evaporated
  7. distillationBulb-to-bulb distillation of the residual pale yellow oil

Sources & evidence

ORD record
ord-49c5d81066de4f88b0e6240724731720
Source dataset
uspto-grants-1999_01
Patent number
US05856309

Reaction notes

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