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

HRID 1670610Notes

Reaction equation

HRID 1670610 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8](OS(C)(=O)=O)[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C)C=O.O>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:22]=[N+:23]=[N-:24])[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Heat a mixture of (2S,4R)-4-methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.60 mol, 185 g) and sodium azide (1.20 mol, 78 g,) in N,N-dimethylformamide (1 L) to 80° C. for 16 h. Dilute the reaction mixture with water and extract with ethyl acetate. Wash the combined organic layers with 0.5 N hydrochloric acid, saturated sodium bicarbonate solution, and brine. Dry over anhydrous sodium sulfate, filter, and concentrate under vacuum to obtain the title compound (140 g, 88%) as a thick, yellow oil. ES-MS m/z 271.2 [M+1]+, 171.0 [M−Boc]+.

Workup

  1. temperatureHeat
  2. extractionextract with ethyl acetate
  3. washWash the combined organic layers with 0.5 N hydrochloric acid, saturated sodium bicarbonate solution, and brine
  4. dry with materialDry over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-857a994234f64303b097fce7710fd0de
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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