Sodium Azide → tert-butyl (3S)-3-aminopiperidine-1-carboxylate

HRID 2113603Notes

Reaction equation

HRID 2113603 reaction equation
[N-:1]=[N+]=[N-].[Na+].CS(O[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1)(=O)=O>CN(C)C=O.O>[NH2:1][C@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 29939737tert-Butyl (3R)-3-[(methanesulfonyl)oxy]piperidine-1-carboxylate

Product 1

HCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium azide (7.65 g, 118 mmol) was added to a solution of 1,1-dimethylethyl (3R)-3-[(methylsulfonyl)oxy]-piperidine-1-carboxylate (21.9 g, 78.5 mmol) in dry dimethylformamide (120 mL) and the resultant suspension heated at 70° C. for 48 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted into ethyl acetate. The organic phase was washed two further times with water, then brine. The organic extracts were dried (MgSO4), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (10:90 to 50:50), to give the title compound as an oil.

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organic phase was washed two further times with water
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give an oil
  7. customThis was purified by flash chromatography on silica
  8. washeluting with ethyl acetate/cyclohexane (10:90 to 50:50)

Sources & evidence

ORD record
ord-78e84d22302c4761b6711cd543c23308
Source dataset
uspto-grants-2008_10
Patent number
US07432280B2

Reaction notes

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