Hydrochloric Acid → 7-Methoxy-4a-methyl-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine

HRID 1616921Notes

Reaction equation

HRID 1616921 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]3([CH3:15])[CH2:12][CH2:11][NH:10][C:9](=O)[CH:8]3[O:14][C:5]=2[CH:4]=1.[AlH4-].[Li+].Cl.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]3([CH3:15])[CH2:12][CH2:11][N:10]=[CH:9][CH:8]3[O:14][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydride2×HCID 673237727-methoxy-4a-methyl-3,4,4a,9a-tetrahydro-2Hbenzo[4,5]furo[2,3-c]pyridine-1-one

Product 1

HCID 673247447-Methoxy-4a-methyl-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methoxy-4a-methyl-3,4,4a,9a-tetrahydro-2Hbenzo[4,5]furo[2,3-c]pyridine-1-one (1.0 g, 4.30 mmol) in tetrahydrofuran (3 mL) was slowly added 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (2 mL). After 30 min stirring another portion of 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (1 mL) was added and the reaction was stirred for 2 h. The reaction was transferred into ice, 6N aqueous HCl was added followed by ethyl acetate. The aqueous layer was basified by adding NaOH and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the solvent was evaporated to provide a colorless oil. The product was used in the next reaction step without further purification.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customto provide a colorless oil
  9. customThe product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-b2c2e0662ec144ac90a842cebd40af0b
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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