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

HRID 1436928Notes

Reaction equation

HRID 1436928 reaction equation
[N-:1]=[N+]=[N-].[Na+].CS(O[C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1)(=O)=O>CN(C)C=O.O>[NH2:1][C@H:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

Product 1

HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium azide (4.4 g, 67.4 mmol) was added to a solution of 1,1-dimethylethyl (3R)-3-[(methylsulfonyl)oxy]-pyrrolidine-1-carboxylate (14.3 g, 54 mmol) in dry dimethylformamide (75 mL) and the resultant suspension heated at 65° C. for 8 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted into diethyl ether. 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 diethyl ether/cyclohexane (20:80 to 40:60), to give the title compound as an oil.

Workup

  1. extractionextracted into diethyl ether
  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 diethyl ether/cyclohexane (20:80 to 40:60)

Sources & evidence

ORD record
ord-9f33e309d80b43f4bf94ec2891fcc0e7
Source dataset
uspto-grants-2009_11
Patent number
US07619096B2

Reaction notes

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