Pyridine → (2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

HRID 1242543Notes

Reaction equation

HRID 1242543 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.Cl.[CH2:19]([O:22][NH2:23])[CH:20]=[CH2:21].N1C=CC=CC=1>C(O)C>[CH2:19]([O:22][N:23]=[C:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:14]([OH:16])=[O:15])[CH2:10]1)[CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid2×HCID 16211718O-Prop-2-en-1-ylhydroxylamine--hydrogen chloride--water (1/1/1)

Product 1

HCID 58714562(2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution was made containing (2S)-1-(tert-butoxycarbonyl)-4-oxo-2-pyrrolidinecarboxylic acid (Intermediate 1, 5.0 g, 22 mmol) and O-allylhydroxylamine hydrochloride monohydrate (7.2 g, 65.5 mmol) in a 1:1 mixture of pyridine and ethanol (100 ml). The reaction was heated to reflux for 2.5 h before cooling and removal of solvent. The residue was dissolved in ethyl acetate and washed rapidly with 1.3N HCl (40 ml). The acidic layer was then extracted with ethyl acetate (3×20 ml) and the combined organic layers washed with brine before drying over magnesium sulfate, filtering and removal of solvent in vacuo. The desired product (5.9 g, 94%) was isolated as a pale yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2.5 h
  3. temperaturebefore cooling
  4. customremoval of solvent
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed rapidly with 1.3N HCl (40 ml)
  7. extractionThe acidic layer was then extracted with ethyl acetate (3×20 ml)
  8. washthe combined organic layers washed with brine
  9. dry with materialbefore drying over magnesium sulfate
  10. filtrationfiltering
  11. customremoval of solvent in vacuo

Sources & evidence

ORD record
ord-e25bdd105f094a92a2614a2391678a3d
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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