Tetrabutylammonium Fluoride → (3S,4R)-3-azido-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1162645Notes

Reaction equation

HRID 1162645 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:10]([N:24]=[N+:25]=[N-:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-:27].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:27])[C@@H:10]([N:24]=[N+:25]=[N-:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58748345(3S,4S)-3-azido-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58748313(3S,4R)-3-azido-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

38.2 A solution of 440 mg (3S,4S)-3-azido-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester in 8.6 ml 1M tetrabutylammonium fluoride solution in THF was stirred overnight at r.t. The reaction mixture was concentrated. The crude product was isolated by column chromatography (silica gel, gradient: cyclohexane->cyclohexane/EtOAc 1:1) to give 150 mg (3S,4R)-3-azido-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester as colorless liquid. MS 230 ([M])

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was isolated by column chromatography (silica gel, gradient: cyclohexane->cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-e61a27cd7b77417794fc637d82c465ee
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

Loading…