Sodium Azide → HCID 10751025, compound

HRID 1885305Notes

Reaction equation

HRID 1885305 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9](OS(C)(=O)=O)[CH2:8][N:7]1[CH2:16][CH3:17])=[O:5])[CH3:2].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C)C=O>[N:18]([C@@H:9]1[CH2:8][N:7]([CH2:16][CH3:17])[C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10]1)=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10491930HCID 10491930, compound

Product 1

HCID 10751025HCID 10751025, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3.5 g of (2S,4R)-2-ethoxycarbonyl-N-ethyl-4-methanesulfonyloxy pyrrolidine, 1.54 g of sodium azide and 10 ml of dimethylformamide was stirred at 90° C. for 4 hours. After cooling, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated under reduced pressure to obtain crude product. This was then subjected to a silica gel column chromatography (elution liq. toluene-ethyl acetate) to obtain pure (2S,4S)-4-azido-2-ethoxycarbonylN-ethyl pyrrolidine as an oily product. Yield 2.05 g.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto obtain crude product
  8. washThis was then subjected to a silica gel column chromatography (elution liq. toluene-ethyl acetate)

Sources & evidence

ORD record
ord-802b261292ce426eb79b0278a13a6188
Source dataset
uspto-grants-1992_09
Patent number
US05143935

Reaction notes

Loading…