Tetrahydrofuran → HCID 9883253, compound

HRID 1383298Notes

Reaction equation

HRID 1383298 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([N:10]3[CH2:15][CH2:14][N:13]([C:16]([CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=O)[CH2:12][CH2:11]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:30]1COCC1>>[CH3:30][N:21]1[CH2:22][CH2:23][CH:18]([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[CH:3]=[CH:2][NH:1]4)[CH2:11][CH2:12]2)[CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 9966545HCID 9966545, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9883253HCID 9883253, compound

Procedure

Under a nitrogen atmosphere, a sample of the carbamate (1.5 g, 3.63 mmol) from example 11 in THF (20 mL) was treated with the dropwise addition of 1.0M lithium aluminium hydride in THF (35 mL, 10 equivalents) at 0° C. and the solution refluxed for 16 hours. After cooling to ambient temperature, the excess hydride was destroyed by the addition of ammonium chloride solution and the mixture filtered. Ethyl acetate (50 mL) was added, the solution washed with water (50 mL), brine (25 mL) and dried over anhydrous sodium sulfate. Filtration and concentration gave the titled product, which was converted to its hydrochloride salt by the action of ethereal-HCl.

Workup

  1. temperaturethe solution refluxed for 16 hours
  2. customthe excess hydride was destroyed by the addition of ammonium chloride solution
  3. filtrationthe mixture filtered
  4. additionEthyl acetate (50 mL) was added
  5. washthe solution washed with water (50 mL), brine (25 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-21450bc6a7da44089c5c8815840219dd
Source dataset
uspto-grants-2001_07
Patent number
US06255302B1

Reaction notes

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