Sodium Azide → (2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

HRID 1527898Notes

Reaction equation

HRID 1527898 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][N:6]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:4].[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:28]=[N+:29]=[N-:30])[CH2:7][N:6]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:4]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 134257721-tert-Butyl 2-methyl (2S,4R)-4-[(4-methylbenzene-1-sulfonyl)oxy]pyrrolidine-1,2-dicarboxylate

Product 1

HCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (14.4 g, 36.09 mmol) in dry N,N-dimethylformamide (50 mL) was added sodium azide (4.7 g, 72.18 mmol) and the reaction mixture was stirred at 60° C. for 16 h. The reaction mixture was diluted with ethyl acetate, washed with water, brine, and dried over anhydrous sodium sulfate. Filtration and concentration gave a crude which was purified by column chromatography (15% ethyl acetate in hexane as eluent) to give (2S,4S)-4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (7.8 g, 80% yield) as a light brown liquid. MS calcd. for C11H19N4O4 [(M+H)+] 271.0, obsd. 271.0.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration
  4. customgave a crude which
  5. customwas purified by column chromatography (15% ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-571ab37064524d14901477c6288dc5f9
Source dataset
uspto-grants-2015_07
Patent number
US09090559B2

Reaction notes

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