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

HRID 1267531Notes

Reaction equation

HRID 1267531 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-b585a81dfc4f4bc1b5395799a9aeb229
Source dataset
uspto-grants-2003_04
Patent number
US06552016B1

Reaction notes

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