Aluminium lithium hydride → HCID 21193307, compound

HRID 1068415Notes

Reaction equation

HRID 1068415 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:14][C:15](=O)[C:16]1([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)C1C=CC=CC=1>CCOCC>[C:25]([O:24][C:22]([N:19]1[CH2:18][CH2:17][C:16]([CH2:15][OH:14])([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:21][CH2:20]1)=[O:23])([CH3:27])([CH3:28])[CH3:26]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54269290HCID 54269290, compound

Product 1

HCID 21193307HCID 21193307, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.32 g, 8.4 mmol) in anhydrous ether (50 ml) was added a solution of 4-(2-methylbenzyl)-N-t-butoxycarbonyl isonipecotic acid benzyl ester (3.0 g, 7.1 mmol) in anhydrous ether (25 ml) over 15 min. The resulting mixture was heated at gentle reflux for 1 hr. The reaction mixture was then quenched with the slow and successive addition of H2O (0.32 ml), 15% aqueous NaOH (0.96 ml), and H2O (0.96 ml). After stirring for 30 min, the mixture was filtered through celite and the filtrate washed with brine, dried (MgSO4), and concentrated in vacuo to a colorless syrup. Purification by chromatography (SiO2, gradient elution, 25 to 50% EtOAc in hexanes), afforded the product as a colorless gum. This material was recrystallized from EtOAc and hexane to afford a white solid. m.p. 104-106° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat gentle reflux for 1 hr
  3. customThe reaction mixture was then quenched with the slow and
  4. additionsuccessive addition of H2O (0.32 ml), 15% aqueous NaOH (0.96 ml), and H2O (0.96 ml)
  5. filtrationthe mixture was filtered through celite
  6. washthe filtrate washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo to a colorless syrup
  9. customPurification
  10. washby chromatography (SiO2, gradient elution, 25 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ae5f8c3160d049ababb11f2395b5bd6c
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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