Quinoline → HCID 58128558, compound

HRID 1039044Notes

Reaction equation

HRID 1039044 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:27])[CH2:11][C:12]#[C:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>CCOC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([O:8][CH2:9][C@H:10]([OH:27])[CH2:11]/[CH:12]=[CH:13]\[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:16][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 58128486HCID 58128486, compound

Product 1

HCID 58128558HCID 58128558, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The alcohol from step 1 of this example (9.1 g, 24.4 mmol) was dissolved in EtOAc (100 ml) and quinoline (0.48 ml, 4.03 mmol) was added. Lindlar's catalyst (1.04 g) was added and the vessel evacuated and refilled three times with H2. The slurry was stirred under a H2 atmosphere for 40 min. The starting material was completely consumed. The mixture was filtered through CELITE and rinsed with EtOAc (4×50 ml). The volume of EtOAc was reduced ˜80% in vacuum. The remaining solution was diluted with ether (100 ml) and washed with 2N HCl (100 ml). The aqueous fraction was re-extracted with ether (2×50 ml), organics combined and washed with 15 ml 2 N HCl. The organic fraction was washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered, and stripped. The resulting oil was purified by chromatography on SiO2 30% eluting with EtOAc:Hexanes to give the titled compound.

Workup

  1. customthe vessel evacuated
  2. additionrefilled three times with H2
  3. customThe starting material was completely consumed
  4. filtrationThe mixture was filtered through CELITE
  5. washrinsed with EtOAc (4×50 ml)
  6. additionThe remaining solution was diluted with ether (100 ml)
  7. washwashed with 2N HCl (100 ml)
  8. extractionThe aqueous fraction was re-extracted with ether (2×50 ml)
  9. washwashed with 15 ml 2 N HCl
  10. washThe organic fraction was washed with saturated aqueous NaHCO3, brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customThe resulting oil was purified by chromatography on SiO2 30%
  14. washeluting with EtOAc

Sources & evidence

ORD record
ord-a269564d2fcd47c595508229615f0da1
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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