HCID 131713906, compound → HCID 20244262, compound

HRID 1632583Notes

Reaction equation

HRID 1632583 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:14])[CH:9]=[C:8]2[C:3]=1[CH:4]([CH2:28][CH2:29][C:30]([O-])=[O:31])[CH2:5][CH:6]1[CH2:27][CH2:26][CH2:25][CH2:24][N:7]12>CCOCC>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:14])[CH:9]=[C:8]2[C:3]=1[CH:4]([CH2:28][CH2:29][CH2:30][OH:31])[CH2:5][CH:6]1[CH2:27][CH2:26][CH2:25][CH2:24][N:7]12

Participants

3

Reactant 1

HCID 131713906HCID 131713906, compound

Product 1

HCID 20244262HCID 20244262, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 125 ml., round bottomed flask equipped with a magnetic stirrer and nitrogen inlet is thoroughly flushed with dry nitrogen. Lithium aluminum hydride, 158 mg. (4.2 mmole) and 50 ml. of dry ethyl ether were added and the suspension stirred and cooled in an ice bath. To the cooled mixture is added slowly 1.89 g. (4.2 mmole) methyl dl-3-[7-hydroxy-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]-quinolin-6-yl]propionate dissolved in 20 ml. of ether. The cooling bath is removed and the reaction mixture is stirred at room temperature for 12 hours. Ethyl acetate, 50 ml., is cautiously added to quench the reaction. The resulting mixture is washed with 50 ml. each of saturated sodium bicarbonate solution, brine and water. The organic layer is dried over anhydrous magnesium sulfate, solvent evaporated in vacuo. The residue is purified by chromatography on silica gel.

Workup

  1. custom, round bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. customis thoroughly flushed with dry nitrogen
  3. additionof dry ethyl ether were added
  4. temperaturecooled in an ice bath
  5. additionTo the cooled mixture is added slowly 1.89 g
  6. customThe cooling bath is removed
  7. stirringthe reaction mixture is stirred at room temperature for 12 hours
  8. addition, is cautiously added
  9. customto quench
  10. customthe reaction
  11. washThe resulting mixture is washed with 50 ml
  12. dry with materialThe organic layer is dried over anhydrous magnesium sulfate, solvent
  13. customevaporated in vacuo
  14. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-69cd433f0c324e49a6af798fd05b617b
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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