2,3,4a,5-Tetrahydro-9-methoxy-4-propyl-4H-[1]-benzopyrano[3,4-b]pyridin-2-one → 9-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine

HRID 364139Notes

Reaction equation

HRID 364139 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:20][CH2:19][CH:10]3[N:11]([CH2:16][CH2:17][CH3:18])[CH2:12][C:13](=O)[CH:14]=[C:9]3[C:7]=2[CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC.C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:20][CH2:19][CH:10]3[N:11]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][CH2:14][CH:9]3[C:7]=2[CH:8]=1

Participants

6

Reactant 2

HCID 201539862,3,4a,5-Tetrahydro-9-methoxy-4-propyl-4H-[1]-benzopyrano[3,4-b]pyridin-2-oneHCID 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 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

9-Methoxy-4-propyl-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridin-2-one is heated with lithium aluminium hydride in ether. The resulting product is hydrogenated in ethanol in the presence of 10% palladium on carbon catalyst to give 9-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine.

Sources & evidence

ORD record
ord-c87b1a2264634b9193c40b1b69b83c1c
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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