tert-Butyl 2-azido-7-azaspiro[3.5]nonane-7-carboxylate → tert-Butyl 2-amino-7-azaspiro(3.5)nonane-7-carboxylate

HRID 336522Notes

Reaction equation

HRID 336522 reaction equation
[N:1]([CH:4]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:5]1)=[N+]=[N-]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C>[NH2:1][CH:4]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:5]1

Participants

4

Reactant 1

HCID 86660638tert-Butyl 2-azido-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 53484529tert-Butyl 2-amino-7-azaspiro(3.5)nonane-7-carboxylate

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

1.85 g (8.97 mmol) of Lindlar catalyst (PdCaCO3) are added to a solution of 4.78 g (17.95 mmol) of tert-butyl 2-azido-7-azaspiro[3.5]nonane-7-carboxylate, obtained in step 2.1., in 70 mL of ethanol. The reaction medium is placed in a Parr flask under a hydrogen atmosphere (20 psi) at room temperature for 5 hours. The resulting mixture is filtered through Celite and the filtrate is then concentrated under reduced pressure. Water and dichloromethane are added. The aqueous phase is separated out and then 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, 3.62 g of product are obtained in the form of an oil, which is used without further purification in the following step.

Workup

  1. customobtained in step 2.1
  2. customat room temperature
  3. customfor 5 hours
  4. filtrationThe resulting mixture is filtered through Celite
  5. concentrationthe filtrate is then concentrated under reduced pressure
  6. additionWater and dichloromethane are added
  7. customThe aqueous phase is separated out
  8. extractionextracted three times with dichloromethane
  9. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. customAfter evaporating off the solvent, 3.62 g of product
  12. customare obtained in the form of an oil, which
  13. customis used without further purification in the following step

Sources & evidence

ORD record
ord-368a7196eb0b48d4b9bc7c00647ea636
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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