Water → HCID 21994146, compound

HRID 1978313Notes

Reaction equation

HRID 1978313 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][C:13]1[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=1)=O)C.C(OCC)(=O)C.O>O1CCCC1>[OH:9][CH2:10][CH2:12][C:13]1[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 21993978HCID 21993978, compound

Product 1

HCID 21994146HCID 21994146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.22 g (32.1 mM) of lithium aluminum hydride in 150 ml of tetrahydrofuran was added a solution of 8.201 g (32.122 mM) of tert-butyl 3-(ethoxycarbonylmethyl)-2,5-dihydropyrrole-1-carboxylate in 50 ml of tetrahydrofuran dropwise under ice-cooling and the mixture was stirred at room temperature for 1 hour. To this reaction mixture was added ethyl acetate with ice-cooling to decompose the excess lithium aluminum hydride, and water was added until a white precipitate had formed. The precipitate was filtered off with the aid of celite and the celite was washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to provide the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionwas added until a white precipitate
  4. customhad formed
  5. filtrationThe precipitate was filtered off with the aid of celite
  6. washthe celite was washed with ethyl acetate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-bc1140f920db4546b147caabd2f3392d
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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