Aluminium lithium hydride → 7-Methyl-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepin-4-ol

HRID 1511604Notes

Reaction equation

HRID 1511604 reaction equation
C(O[C:4]([N:6]1[CH2:12][CH2:11][C:10](=[O:13])[C:9]2[CH:14]=[CH:15][O:16][C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:4][N:6]1[CH2:12][CH2:11][CH:10]([OH:13])[C:9]2[CH:14]=[CH:15][O:16][C:8]=2[CH2:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 68409591HCID 68409591, compound

Product 1

HCID 684096967-Methyl-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepin-4-olYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.38 g of 7-ethoxycarbonyl-5,6,7,8-tetrahydrofuro[2,3-c]azepin-4-one prepared in the step 5 in 30 mL of dry THF was slowly added by dropping into an ice-cooled solution of 0.29 g of lithium aluminum hydride in 20 mL of dry THF. The reaction solution was gradually heated followed by heating to reflux for 30 minutes. The reaction solution was cooled, an excess of lithium aluminum hydride was decomposed by gradual addition of ice thereto and the reaction solution was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 0.45 g of the objective compound.

Workup

  1. additionwas slowly added
  2. temperatureThe reaction solution was gradually heated
  3. temperatureby heating
  4. temperatureto reflux for 30 minutes
  5. temperatureThe reaction solution was cooled
  6. extractionthe reaction solution was subjected to extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2a1a2cdd18d34300be81cd7525828a90
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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