Sodium Azide → (2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester

HRID 1594239Notes

Reaction equation

HRID 1594239 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[C@@H:6]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:8]([C:18]([O:20][CH3:21])=[O:19])[CH2:7]1>CN(C)C=O>[N:1]([C@H:6]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:8]([C:18]([O:20][CH3:21])=[O:19])[CH2:7]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 34176502(2S,4S)-1-tert-butyl 2-methyl 4-bromopyrrolidine-1,2-dicarboxylate

Product 1

HCID 11369242(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl EsterYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dispersion of sodium azide (0.90 g, 13.84 mmol) and 1-(tert-butyl)-2-methyl (2S,4S)-4-bromotetrahydro-1H-1,2-pyrroledicarboxylate (4) (1.0 g, 3.24 mmol) in anhydrous dimethylformamide (32 mL) was heated for 64 h under an atmosphere of nitrogen. The mixture was cooled to room temperature, poured into ice-cold water and extracted with ethyl acetate. The organic extracts were combined, washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with hexane-ethyl acetate (3:1 to 1:1, v/v) to give the title azide (5) (0.88 g, 93%) as a pale yellow oil:

Workup

  1. additionpoured into ice-cold water
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography
  7. washeluting with hexane-ethyl acetate (3:1 to 1:1

Sources & evidence

ORD record
ord-0d5183f865a94fec95be622240dc0ee4
Source dataset
uspto-grants-2007_11
Patent number
US07300929B2

Reaction notes

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