Triethylamine → tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 538734Notes

Reaction equation

HRID 538734 reaction equation
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C([O-])(=O)C.[NH4+:19].C([N:22](CC)[CH2:23][CH3:24])C>>[NH:19]1[CH:24]=[CH:23][N:22]=[C:1]1[C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 49783269tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylateYield 136.9%

Conditions

Temperature
140 °C

Procedure

A mixture of 4 (11.09 g, 25.3 mmol), ammonium acetate (29.25 g, 38.0 mmol) and triethylamine (38.45 g, 38.0 mmol) in xylenes (600 mL) in a sealed tube was stirred at 140° C. for 2 h. After being cooled, the reaction mixture was transferred into a flask and concentrated to dryness. The residue was partitioned between chloroform and H2O, and the organic layer was washed with H2O and concentrated. The crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v)) to afford 5 (8.22 g, 75% yield) as a white solid. LC-MS (ESI): m/z 420.1 (M+H)+.

Workup

  1. temperatureAfter being cooled
  2. customthe reaction mixture was transferred into a flask
  3. concentrationconcentrated to dryness
  4. customThe residue was partitioned between chloroform and H2O
  5. washthe organic layer was washed with H2O
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v))

Sources & evidence

ORD record
ord-c8e851cf96fe452094a34537bcb3aecf
Source dataset
uspto-grants-2014_10
Patent number
US08865756B2

Reaction notes

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