Sodium Hydroxide → tert-Butyl 2-(aminomethyl)-7-azaspiro[3.5]nonane-7-carboxylate

HRID 336523Notes

Reaction equation

HRID 336523 reaction equation
[C:1]([CH:3]1[CH2:6][C:5]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:4]1)#[N:2].[OH-].[Na+]>C(O)C.[Ni]>[NH2:2][CH2:1][CH:3]1[CH2:6][C:5]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11172744Tert-butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 56962135tert-Butyl 2-(aminomethyl)-7-azaspiro[3.5]nonane-7-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.40 g (5.59 mmol) of tert-butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate (Chem. Pharm. Bull.; 52 (6), 675-687, 2004), in 10 mL of a 1N solution of sodium hydroxide in ethanol. 0.164 g (2.80 mmol) of Raney nickel is then added. The reaction medium is placed in a Parr flask under a hydrogen atmosphere (60 psi) at room temperature for 2 hours. The resulting mixture is filtered through a Büchner funnel and the filtrate is then concentrated under reduced pressure. Dichloromethane is added, the aqueous phase is separated out and extracted three times with dichloromethane, and the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. After evaporating off the solvent, 1.212 g of product are obtained in the form of a colourless oil, which is used without further purification in the following step.

Workup

  1. customat room temperature
  2. customfor 2 hours
  3. filtrationThe resulting mixture is filtered through a Büchner funnel
  4. concentrationthe filtrate is then concentrated under reduced pressure
  5. additionDichloromethane is added
  6. customthe aqueous phase is separated out
  7. extractionextracted three times with dichloromethane
  8. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. customAfter evaporating off the solvent, 1.212 g of product
  11. customare obtained in the form of a colourless oil, which
  12. customis used without further purification in the following step

Sources & evidence

ORD record
ord-0e03d73374714eb69ff4b2e1e9360952
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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