Sodium Hydroxide → 5-Benzyl-5-azaspiro[2.4]heptan-7-amine

HRID 1366514Notes

Reaction equation

HRID 1366514 reaction equation
CO/[N:3]=[C:4]1\[CH2:5][N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7](=O)[C:8]2\1[CH2:10][CH2:9]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[C:13]1([CH2:12][N:6]2[CH2:5][CH:4]([NH2:3])[C:8]3([CH2:9][CH2:10]3)[CH2:7]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 87210371(7Z)-5-benzyl-7-methoxyimino-5-azaspiro[2.4]heptan-4-one

Product 1

HCID 108565665-Benzyl-5-azaspiro[2.4]heptan-7-amineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (7Z)-5-(phenylmethyl)-5-azaspiro[2.4]heptane-4,7-dione 7-(O-methyloxime) (assumed 3.1553 g, 12.92 mmol) in THF (130 mL) was added lithium aluminum hydride (1.58 g, 41.63 mmol). The mixture was heated at 65° C. and stirred for 3 h. The mixture was then cooled to 0° C., and Na2SO4.10H2O was added. The mixture was stirred overnight, and then 1 N aq. NaOH (6 mL) was added. The mixture was vigorously stirred for 30 min, and then extracted with DCM (3×50 mL). The combined organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide racemic crude 5-(phenylmethyl)-5-azaspiro[2.4]heptan-7-amine (2.5355 g, 97% for 2 steps) as a light yellow oil. LCMS: (M+H)+: 203.1.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. stirringThe mixture was stirred overnight
  3. stirringThe mixture was vigorously stirred for 30 min
  4. extractionextracted with DCM (3×50 mL)
  5. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ad4979f3fc747ebbd908b30ce045e29
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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