HCID 20153968, compound → 9-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine

HRID 2414178Notes

Reaction equation

HRID 2414178 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:26][CH2:25][CH:16]3[N:17]([C:21](=O)[CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH:15]3[C:13]=2[CH:14]=1>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:26][CH2:25][CH:16]3[N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH:15]3[C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 20153968HCID 20153968, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 141515789-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3.8 g of lithium aluminum hydride in a 100 ml of tetrahydrofuran, 3,6 g of concentrated sulfuric, acid is first added dropwise at -5° to -10°, then 5.0 g of 9-methoxy-4-propionyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine is added slowly with stirring. The reaction mixture is allowed to warm to room temperature, stirred for 18 hours and finally heated under reflux for 1 hour. After cooling the reaction mixture is quenched with ethyl acetate, then treated with a small volume of water and 3N sodium hydroxide, filtered and concentrated in vacuo. The residue is redissolved in ethyl acetate and the ethyl acetate solution is washed with water, dried and evaporated to yield 9-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine.

Workup

  1. additionis first added dropwise at -5° to -10°
  2. stirringstirred for 18 hours
  3. temperaturefinally heated
  4. temperatureunder reflux for 1 hour
  5. temperatureAfter cooling the reaction mixture
  6. customis quenched with ethyl acetate
  7. additiontreated with a small volume of water and 3N sodium hydroxide
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue is redissolved in ethyl acetate
  11. washthe ethyl acetate solution is washed with water
  12. customdried
  13. customevaporated

Sources & evidence

ORD record
ord-ddad0af6b1ac49f985c6abb84b1dfbd2
Source dataset
uspto-grants-1988_01
Patent number
US04721787

Reaction notes

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