Water → HCID 19960978, compound

HRID 53880Notes

Reaction equation

HRID 53880 reaction equation
[CH2:1]([N:8]1[CH2:15][C:14]2([C:16]#[N:17])[CH:10]([CH2:11][O:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:17][CH2:16][C:14]12[CH2:15][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH:10]1[CH2:11][O:12][CH2:13]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19960963HCID 19960963, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19960978HCID 19960978, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.7 g (15.9 mmol) of 7-benzyl-1-cyano-3-oxa-7-azabicyclo[3.3.0]octane in 5 ml of absolute tetrahydrofuran are added dropwise to a mixture of 1.5 g of lithium aluminium hydride in 100 ml of absolute tetrahydrofuran and the resulting mixture is heated under reflux for 15 hours. Decomposition is effected with 1.5 ml each of water, 15% strength sodium hydroxide solution, and again water, and the mixture is filtered with suction, and the aluminium salts are extracted by boiling on two occasions with 100 ml of tetrahydrofuran. The tetrahydrofuran solutions are concentrated and the residue is distilled. Yield: 3.2 g (86% of theory) Boiling point: 125°-130° C./0.04 mbar

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 15 hours
  3. filtrationthe mixture is filtered with suction
  4. extractionthe aluminium salts are extracted
  5. concentrationThe tetrahydrofuran solutions are concentrated
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-d37da7198475475b83000f1d89aa6a2d
Source dataset
uspto-grants-1997_04
Patent number
US05621105

Reaction notes

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