Trifluoroacetic acid → (2S,4R)-2-Azidomethyl-4-fluoro-pyrrolidine

HRID 1527382Notes

Reaction equation

HRID 1527382 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][N:15]=[N+:16]=[N-:17])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:15]([CH2:14][C@@H:9]1[CH2:10][C@@H:11]([F:13])[CH2:12][NH:8]1)=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673832HCID 86673832, compound

Product 1

HCID 86673833(2S,4R)-2-Azidomethyl-4-fluoro-pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-2-azidomethyl-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (600 mg, 2.45 mmol) in CH2Cl2 (2.5 mL) was added TFA (1.88 mL, 24.6 mmol) and the solution was stirred at RT for 2 h. CH2Cl2 was concentrated and the crude was dried under high vacuum to give the desired material which was used without further purification in the next step.

Workup

  1. concentrationCH2Cl2 was concentrated
  2. customthe crude was dried under high vacuum

Sources & evidence

ORD record
ord-68646736dd584fda86226b06b63909c7
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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