5,5-dimethyl-8-[5-(4-fluorophenyl)-2-pentyl]-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine → 5,5-Dimethyl-8-[5-(4-fluorophenyl)-2-pentyl]-10-hydroxy-5H-[1]benzopyrano[3,4-d]pyridine

HRID 126808Notes

Reaction equation

HRID 126808 reaction equation
[CH3:1][C:2]1([CH3:29])[C:24]2[CH2:25][CH2:26][NH:27][CH2:28][C:23]=2[C:5]2[C:6]([OH:22])=[CH:7][C:8]([CH:10]([CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH3:11])=[CH:9][C:4]=2[O:3]1>[Pd].C1(C)C(C)=CC=CC=1>[CH3:29][C:2]1([CH3:1])[C:24]2=[CH:25][CH:26]=[N:27][CH:28]=[C:23]2[C:5]2[C:6]([OH:22])=[CH:7][C:8]([CH:10]([CH2:12][CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH3:11])=[CH:9][C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 128007415,5-dimethyl-8-[5-(4-fluorophenyl)-2-pentyl]-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine

Product 1

HCID 202878485,5-Dimethyl-8-[5-(4-fluorophenyl)-2-pentyl]-10-hydroxy-5H-[1]benzopyrano[3,4-d]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 4.75 g. of 5,5-dimethyl-8-[5-(4-fluorophenyl)-2-pentyl]-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, 1.0 g. of 10% palladium on carbon, and 120 ml. of xylene was stirred and refluxed for 22 hours. After removal of the catalyst, the filtrate was evaporated in vacuo and the residue was purified by chromatography on a Florisil column (150 g.). The column was first eluted with chloroform, followed by 5% methanol in chloroform to give the pure product; m.p. 72°-74°.

Workup

  1. additionA mixture of 4.75 g
  2. temperaturerefluxed for 22 hours
  3. customAfter removal of the catalyst
  4. customthe filtrate was evaporated in vacuo
  5. customthe residue was purified by chromatography on a Florisil column (150 g.)
  6. washThe column was first eluted with chloroform
  7. customto give the pure product

Sources & evidence

ORD record
ord-5cdbb68bada241f4bb1b517fe52c2adf
Source dataset
uspto-grants-1981_03
Patent number
US04254116

Reaction notes

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