tert-Butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylate → tert-Butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate

HRID 336527Notes

Reaction equation

HRID 336527 reaction equation
[N:1]([CH:4]1[CH2:7][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[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[CH2:5][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:7]1

Participants

4

Reactant 1

HCID 86660640tert-Butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylate

Product 1

HCID 56962195tert-Butyl 2-amino-6-azaspiro[3.4]octane-6-carboxylate

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

1.50 g (7.27 mmol) of Lindlar catalyst (PdCaCO3) are added to a solution of 3.67 g (14.54 mmol) of tert-butyl 2-azido-6-azaspiro[3.4]octane-6-carboxylate, obtained in step 6.3., in 60 mL of ethanol. The reaction medium is placed in a Parr flask under a hydrogen atmosphere at 20 psi, at room temperature for 5 hours. The resulting mixture is filtered through Celite and the filtrate is then concentrated under reduced pressure. After evaporating off the solvent, the residue obtained is purified by chromatography on silica gel, eluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia.

Workup

  1. customobtained in step 6.3
  2. filtrationThe resulting mixture is filtered through Celite
  3. concentrationthe filtrate is then concentrated under reduced pressure
  4. customAfter evaporating off the solvent
  5. customthe residue obtained
  6. customis purified by chromatography on silica gel
  7. washeluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-50126bcdd4434443bf40d7ba3b9ee9bd
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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