Sodium Carbonate → HCID 15430829, compound

HRID 430819Notes

Reaction equation

HRID 430819 reaction equation
P(Cl)(Cl)(Cl)=O.CC(C)=O.C(=O)=O.[C:13]([C:15]1(O)[CH2:21][CH:20]2[N:22]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH:17]([CH2:18][CH2:19]2)[CH2:16]1)#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.N1C=CC=CC=1>[C:13]([C:15]1[CH2:16][CH:17]2[N:22]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH:20]([CH2:19][CH2:18]2)[CH:21]=1)#[N:14]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 18316935HCID 18316935, compoundHCID 18522661Acetone cardice

Product 1

HCID 15430829HCID 15430829, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
28 °C

Procedure

An oven-dried 100 ml 3-necked round bottom flask was fitted with a reflux condenser, thermometer and magnetic stirrer and the apparatus filled with a nitrogen atmosphere. Phosphorous oxychloride (8.89 g, 58 mmol) and pyridine (44 ml) were charged and the mixture then cooled to −10° C. in an acetone/Drikold™ bath. 3-Cyano-3-hydroxy-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane (6.17 g, 26.4 mmol—assumed) was added in one portion and the resulting exotherm raised the reaction mass temperature to 28° C. The mixture was then heated to 80° C. and held at this temperature overnight. The reaction mass was cooled to ambient (precipitation occurred) and added to a stirred mixture of saturated aqueous sodium carbonate (200 ml) and ethyl acetate (200 ml). The layers were separated and the aqueous then extracted with ethyl acetate (2×200 ml). The combined organics were washed with brine (100 ml), dried (Na2SO4) and concentrated in vacuo to give 3-cyano-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1 ]oct-2-ene (2.5 g, 35% yield).

Workup

  1. customAn oven-dried 100 ml 3-necked round bottom flask was fitted with a reflux condenser
  2. additionthermometer and magnetic stirrer and the apparatus filled with a nitrogen atmosphere
  3. temperatureThe mixture was then heated to 80° C.
  4. customheld at this temperature overnight
  5. temperatureThe reaction mass was cooled to ambient (precipitation occurred)
  6. customThe layers were separated
  7. extractionthe aqueous then extracted with ethyl acetate (2×200 ml)
  8. washThe combined organics were washed with brine (100 ml)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a1cc6274b4347afb228f2ad44ee1386
Source dataset
uspto-grants-2001_11
Patent number
US06323343B1

Reaction notes

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