Ethanol → HCID 12151259, compound

HRID 353374Notes

Reaction equation

HRID 353374 reaction equation
O=[C:2]1[CH:7]2[CH2:8][C:4]3([C:9]([OH:11])=[O:10])[CH:5]([CH2:6]2)[CH:3]13.[C-]#N.[K+].[C:15](=[O:18])([O-])[O-].[NH4+:19].[NH4+:20].[CH2:21]([OH:23])C>C(O)C.O>[O:23]=[C:21]1[NH:20][C:2]2([CH:7]3[CH2:8][C:4]4([C:9]([OH:11])=[O:10])[CH:5]([CH2:6]3)[CH:3]24)[C:15](=[O:18])[NH:19]1

Participants

6

Reactant 4

HCID 702EthanolHCID 9032Potassium Cyanide2×HCID 517111Ammonium Carbonate2×HCID 1215125822630-90-6

Product 1

HCID 12151259HCID 12151259, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1.52 g (10 mmole) of 3-oxo-tricyclo[2.2.1.02,6]heptane-1-carboxylic acid, 0.78 g (12 mmole) of potassium cyanide and 3.36 g (35 mmole) of ammonium carbonate in 75 mL of ethanol-water (1:1) was stirred at 75° C. for 18 hours. An additional 2-4 mmole of potassium cyanide and 6-12 mmole of ammonium carbonate were added and stirring at 75° C. was continued for 18 hours. The ethanol was then allowed to evaporate and the reaction mixture adjusted to pH 1 with concentrated HCl. Upon cooling the mixture to 0° C., a white precipitate formed and was removed by filtration and washed with ice-cold water and ethyl acetate and dried in vacuum to give 1.32 g of the title compound. Concentration of the mother liquor led to the isolation of an additional 0.22 g of white solid. Thus, 1.54 g of the title compound were obtained as a mixture of diastereomers.

Workup

  1. stirringstirring at 75° C.
  2. waitwas continued for 18 hours
  3. customto evaporate
  4. temperatureUpon cooling the mixture to 0° C.
  5. customa white precipitate formed
  6. customwas removed by filtration
  7. washwashed with ice-cold water and ethyl acetate
  8. customdried in vacuum

Sources & evidence

ORD record
ord-22442a4879194c9db7961f46353e1d2f
Source dataset
uspto-grants-2004_06
Patent number
US06750364B2

Reaction notes

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