Tert-butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate → tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate

HRID 336544Notes

Reaction equation

HRID 336544 reaction equation
[N:1]([CH:4]1[CH2:17][C:6]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]2)[CH2:5]1)=[N+]=[N-]>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:1][CH:4]1[CH2:5][C:6]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:7]2)[CH2:17]1

Participants

4

Reactant 1

HCID 86660643Tert-butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate

Product 1

HCID 46930560tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

The process is performed according to the procedure described in Example 6 (step 6.4.). Starting with 0.638 g (2.68 mmol) of tert-butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate, obtained in step 11.5., in 11 mL of ethanol, 0.276 g (1.34 mmol) of Lindlar catalyst (PdCaCO3) is added. After purification on a column of silica gel, eluting with a 98/2/0.2 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.330 g of pure product is obtained in the form of a white powder.

Workup

  1. customobtained in step 11.5
  2. customAfter purification on a column of silica gel
  3. washeluting with a 98/2/0.2 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-3053c72c190e42dd8cf8fac4b2fefe64
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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