1,1'-Carbonyldiimidazole → 1-[3-(3,4-Dichlorophenyl)-5-hydroxy-1-oxopentyl]-1,2,3,4-tetrahydroquinoline

HRID 2256311Notes

Reaction equation

HRID 2256311 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14]C(=O)C2CCC3C(=CC=CC=3)N2)[CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:27]([N:34]1[CH:38]=[CH:37]N=[CH:35]1)(N1C=CN=C1)=[O:28].[BH4-].[Na+]>CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:12])[CH2:14][C:27]([N:34]2[C:35]3[C:6](=[CH:7][CH:2]=[CH:3][CH:4]=3)[CH2:5][CH2:37][CH2:38]2)=[O:28])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 19029335HCID 19029335, compound

Product 1

HCID 190293711-[3-(3,4-Dichlorophenyl)-5-hydroxy-1-oxopentyl]-1,2,3,4-tetrahydroquinolineYield 166.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Beta-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-delta-oxo-quinolinepentanoic acid (14.3 g) in EtOAc (300 mL) was treated with carbonyldiimidazole (7.42 g) and N,N-dimethylaminopyridine (450 mg). The resulting solution was stirred at room temperature for 15 minutes and then heated at 50° C. for two hours. The reaction mixture was cooled to 0° C. and treated with a solution of NaBH4 (5.5 g) in H2O (100 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was diluted with EtOAc (500 mL) and washed with 1N HCl (1×200 mL), sat. NaHCO3 (1×200 mL) and water (1×200 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to yield the crude compound as a oil. Silica gel chromatography eluting with 0-10% MeOH/CH2Cl2 gave the title compound (11.5 g). Mass spectrum (CI): 378.

Workup

  1. temperatureheated at 50° C. for two hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. temperaturewarmed slowly to room temperature
  4. stirringstirred for 12 hours
  5. washwashed with 1N HCl (1×200 mL), sat. NaHCO3 (1×200 mL) and water (1×200 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield the crude compound as a oil
  10. washSilica gel chromatography eluting with 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1e1954af544e43818f2e7ecd13428893
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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