Potassium Carbonate → HCID 86668652, compound

HRID 73611Notes

Reaction equation

HRID 73611 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]#[N:18])[C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li].[CH2:20]([O:22][CH:23]=[CH2:24])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH2:1]([N:8]([CH2:16][C:17]#[N:18])[C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@:10]1([C:20]([O:22][CH2:23][CH3:24])=[CH2:21])[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86668650HCID 86668650, compoundHCID 86668653HCID 86668653, compound

Product 1

HCID 86668652HCID 86668652, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To {benzyl[(1R)-2-oxocyclohexyl]amino}acetonitrile (298 mg, 1.230 mmol) in THF (9 ml) at −78° C. was added ethylvinyl ether lithium (7.38 ml, 3.69 mmol) in THF via a cannula dropwise over 25 min. The reaction mixture was stirred for an addition 40 min at −78° C. before wet THF (THF/Water 10/1, 10 ml) was added. The reaction was allowed to warm to room temperature. The mixture was cooled, aqueous potassium carbonate (saturated, 10 mL) was added and the mixture was extracted with ethyl acetate (3×20 mL). The combined organic fractions were washed with brine (saturated, 30 mL), dried, filtered and the solvent was evaporated under reduced pressure to give the title compound. The crude product was used directly without further purification in the next step.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled
  3. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  4. washThe combined organic fractions were washed with brine (saturated, 30 mL)
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-94ecfcfedb2a49299be9194fe9b496ee
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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