Trifluoroacetic acid → (2S)-2-[(2-Chloro-5-nitrophenoxy)methyl]pyrrolidine

HRID 491592Notes

Reaction equation

HRID 491592 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[Cl:24])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:24][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 17755966HCID 17755966, compound

Product 1

HCID 17755967(2S)-2-[(2-Chloro-5-nitrophenoxy)methyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(2-Chloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (6.94 g, 19.45 mmol) was stirred in 30 mL CH2Cl2 and 20 ml TFA for 3 h. The reaction was concentrated and dissolved in 0.1 N HCl (aq), which was basified to pH>12 with solid NaOH and extracted 3× with EtOAc. The organic layers were washed once with 1 N NaOH then once with a mixture of brine and 1 N NaOH. The organic layers were combined, dried over Na2SO4, filtered, and concentrated to dryness, to yield the title compound as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in 0.1 N HCl (aq)
  3. extractionextracted 3× with EtOAc
  4. washThe organic layers were washed once with 1 N NaOH
  5. additiononce with a mixture of brine and 1 N NaOH
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8174b9d4c373464b87a7f6dde7fe49a6
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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