Sodium hydride → 3-Cyclopropyl-2-oxopyrrolidine-3-carbonitrile

HRID 714814Notes

Reaction equation

HRID 714814 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([C:20]#[N:21])([CH:17]1[CH2:19][CH2:18]1)[C:12](OCC)=[O:13])=O)(C)(C)C.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH:17]1([C:11]2([C:20]#[N:21])[CH2:10][CH2:9][NH:8][C:12]2=[O:13])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 117840908Ethyl 4-((tert-butoxycarbonyl)amino)-2-cyano-2-cyclopropylbutanoate

Product 1

HCID 916186313-Cyclopropyl-2-oxopyrrolidine-3-carbonitrileYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-((tert-butoxycarbonyl)amino)-2-cyano-2-cyclopropylbutanoate (45 g) obtained in Step B of Example 103 in tetrahydrofuran (1.2 L) was added sodium hydride (60% in mineral oil, 7.3 g) in an ice bath, and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution (100 mL), the solvent (tetrahydrofuran) was evaporated under reduced pressure, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (18 g).

Workup

  1. customthe solvent (tetrahydrofuran) was evaporated under reduced pressure
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d4c9bb5079294c429cb13d3313aacb85
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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