Water → 7-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane

HRID 389248Notes

Reaction equation

HRID 389248 reaction equation
[NH2:1][C:2]1([CH3:17])[C:6]2([CH2:8][CH2:7]2)[C:5](=O)[N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[NH2:1][C:2]1([CH3:17])[C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 575873067-Amino-5-benzyl-4-oxo-7-methyl-5-azaspiro[2.4]heptane

Product 1

HCID 249623127-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptaneYield 98.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Amino-5-benzyl-4-oxo-7-methyl-5-azaspiro[2.4]heptane (27 g) was dissolved in anhydrous tetrahydrofuran (265 mL) in an argon atmosphere, and the solution was cooled with ice. Lithium aluminum hydride (13.3 g) was added thereto, and the mixture was returned to room temperature. After disappearance of the starting materials had been confirmed, the reaction mixture was cooled with ice. Water (200 mL) and 28% aqueous sodium hydroxide solution (70 mL) were added to cooled mixture, followed by stirring. Toluene was added to the mixture for extraction to separate the organic layer, and the organic layer was washed with saturated brine, followed by drying with sodium sulfate. The desiccant was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield the title product (24.7 g, yield: 98.6%).

Workup

  1. temperaturethe solution was cooled with ice
  2. customwas returned to room temperature
  3. temperaturethe reaction mixture was cooled with ice
  4. temperatureto cooled mixture
  5. customto separate the organic layer
  6. washthe organic layer was washed with saturated brine
  7. dry with materialby drying with sodium sulfate
  8. customThe desiccant was removed through filtration
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-34f45a26566e4bf59024b981fad880cd
Source dataset
uspto-grants-2013_02
Patent number
US08378119B2

Reaction notes

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