2-Benzyl-2-azaspiro[4.4]nonane-1,4-dione → 2-Benzyl-2-azaspiro[4.4]nonan-4-ol

HRID 1477944Notes

Reaction equation

HRID 1477944 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11](=[O:13])[C:10]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:13])[C:10]2([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 107053912-Benzyl-2-azaspiro[4.4]nonane-1,4-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 1183900852-Benzyl-2-azaspiro[4.4]nonan-4-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a cooled to 0° C. solution of 2-benzyl-2-azaspiro[4.4]nonane-1,4-dione (20.00 g, 82.2 mmol) in THF (150 mL) was added LiAlH4 (20.93 g, 550.8 mmol) portionwise. After addition, the reaction mixture was stirred at 80° C. overnight, cooled down to rt and quenched carefully with sequential addition of EtOAc (200 mL), 15% KOH aqueous solution (40 mL) and water (100 mL). After addition, the resulting mixture was stirred at rt for 3 h, and filtered through a Celite pad, then washed with EtOAc (1 L). The filtrate was concentrated in vacuo to give the product as yellow oil (19.02 g, 100%).

Workup

  1. additionAfter addition
  2. temperaturecooled down to rt
  3. customquenched carefully with sequential addition of EtOAc (200 mL), 15% KOH aqueous solution (40 mL) and water (100 mL)
  4. additionAfter addition
  5. stirringthe resulting mixture was stirred at rt for 3 h
  6. filtrationfiltered through a Celite pad
  7. washwashed with EtOAc (1 L)
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-191de252f2c94a75962e5f819af13d51
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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