Water → HCID 22475179, compound

HRID 2103112Notes

Reaction equation

HRID 2103112 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[O:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]([N:24]4[CH2:29][CH:28]=[C:27]([C:30]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=5)[CH2:26][CH2:25]4)=O)=[CH:21][C:15]=3[O:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:37]1([C:13]2([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:17][C:16]3[CH:18]=[CH:19][C:20]([CH2:22][N:24]4[CH2:25][CH:26]=[C:27]([C:30]5[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=5)[CH2:28][CH2:29]4)=[CH:21][C:15]=3[O:14]2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10344962HCID 10344962, compoundHCID 21226445Aluminium lithium hydride3×

Product 1

HCID 22475179HCID 22475179, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Lithium aluminium hydride (13 mg, 0.36 mmol) was suspended in THF (10 ml). At room temperature (2,2-Diphenyl-benzo[1,3]dioxol-5-yl)-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-methanone (104 mg, 0.22 mmol) dissolved in THF (1.5 ml) was added dropwise under argon. The reaction was heated to reflux for 2 hours. Lithium aluminium hydride (50 mg) was added and the reaction was heated to reflux overnight under argon. Lithium aluminium hydride solution (0.3 ml, 1M solution in THF) was added and the reaction heated to reflux for 4 hours. The reaction was cooled (ice bath) and under argon a mixture of water (0.4 ml) and THF (1.5 ml) was added slowly. The reaction was stirred for 10 minutes and solid potassium carbonate (2 g) was added. The reaction was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate. The organic solution was dried over sodium sulfate, filtered and the solvent was evaporated to yield the product as a white colorless viscous oil (85 mg, 85%).

Workup

  1. additionwas added dropwise under argon
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hours
  4. temperaturethe reaction was heated
  5. temperatureto reflux overnight under argon
  6. temperaturethe reaction heated
  7. temperatureto reflux for 4 hours
  8. temperatureThe reaction was cooled (ice bath)
  9. additionwas added slowly
  10. filtrationThe reaction was filtered
  11. concentrationthe filtrate was concentrated in vacuo
  12. dissolutionThe residue was dissolved in ethyl acetate
  13. dry with materialThe organic solution was dried over sodium sulfate
  14. filtrationfiltered
  15. customthe solvent was evaporated

Sources & evidence

ORD record
ord-29fea033749b45588c0b6c726913f9fd
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

Loading…