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

HRID 2078378Notes

Reaction equation

HRID 2078378 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-9cc32a9cbe9f4fb3a7246ba2a8bb11bc
Source dataset
uspto-grants-2011_04
Patent number
US07928232B2

Reaction notes

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