2-Oxopropiononitrile → HCID 59679471, compound

HRID 2354865Notes

Reaction equation

HRID 2354865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]3[CH2:17][CH2:18][CH2:19][CH:12]2[CH2:13][C:14](=[O:20])[CH2:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[C:29](#N)[C:30](C)=[O:31]>C1COCC1>[C:30]([CH:15]1[C:14](=[O:20])[CH2:13][CH:12]2[N:11]([S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[CH:16]1[CH2:17][CH2:18][CH2:19]2)(=[O:31])[CH3:29]

Participants

5

Reactant 3

HCID 694302-OxopropiononitrileHCID 2724682Lithium diisopropylamideHCID 161174379-(4-Chlorobenzene-1-sulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

Product 1

HCID 59679471HCID 59679471, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ketone (9-[(4-chlorophenyl)sulfonyl]-9-azabicyclo[3.3.1]nonan-3-one, 94 mg, 0.30 mmol) under nitrogen was dissolved in THF (1.5 mL), and with good stirring at room temperature, lithium diisopropylamide (1.0 M in cyclohexane/THF, 1.0 mL, 1.0 mmol) was added all at once by syringe. After stirring for 15 min, pyruvonitrile (140 mg, 2.0 mmol) was added all at once to the reaction mixture and stirred vigorously for 30 min at RT and for 24 h in a 60° C. bath. The reaction mixture was partially evaporated under a stream of nitrogen while being warmed in a 70° C. bath. The black residue was dissolved with water and dichloromethane and acidified with aq NaHSO4. The organic phase was separated and combined with one additional dichloromethane extraction of the aq phase. The organic phase was washed with 0.1 M NaOH (3×), and the basic washes were combined and acidified to pH 1-2 using aq NaHSO4. The acidic phase was extracted with dichloromethane (3×), and the combined dichloromethane extracts were washed with brine (2×), and then dried (Na2SO4) and evaporated to yield the brown solid product. MS (ES) m/e 356.0 (M+H)+.

Workup

  1. stirringAfter stirring for 15 min
  2. stirringstirred vigorously for 30 min at RT and for 24 h in a 60° C. bath
  3. customThe reaction mixture was partially evaporated under a stream of nitrogen
  4. temperaturewhile being warmed in a 70° C. bath
  5. dissolutionThe black residue was dissolved with water and dichloromethane
  6. customThe organic phase was separated
  7. extractioncombined with one additional dichloromethane extraction of the aq phase
  8. washThe organic phase was washed with 0.1 M NaOH (3×)
  9. extractionThe acidic phase was extracted with dichloromethane (3×)
  10. washthe combined dichloromethane extracts were washed with brine (2×)
  11. dry with materialdried (Na2SO4)
  12. customevaporated
  13. customto yield the brown solid product

Sources & evidence

ORD record
ord-48074a58885344909d5e37cb76ec12e7
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

Loading…