Sodium Azide → 3-(1-Azidoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl ester

HRID 10355Notes

Reaction equation

HRID 10355 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([F:23])([CH:16](OS(C)(=O)=O)[CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([CH:16]([N:24]=[N+:25]=[N-:26])[CH3:17])([F:23])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 866071353-Fluoro-3-(1-methanesulfonyloxyethyl)pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 866071343-(1-Azidoethyl)-3-fluoropyrrolidine-1-carboxylic acid benzyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-fluoro-3-(1-methanesulfonyloxyethyl)pyrrolidine-1-carboxylic acid benzyl ester (Example A15, 0.25 g, 0.72 mmol) in N,N-dimethylformamide (5 mL) is added sodium azide (0.13 g, 2 mmol). The reaction mixture is heated at 120° C. overnight. The mixture is diluted with water and extracted with ethyl acetate. The extracts are washed with brine, dried over Na2SO4 and concentrated to afford the title compound (0.160 g). 1H NMR (200 MHz, CDCl3): δ 7.28 (s, 5H), 5.08 (s, 2H), 3.80–3.25 (m, 5H), 2.13–1.75 (m, 2H), 1.40 (d, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28a8f740c3c44d56886c2f08e9774695
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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