Acetic Acid → HCID 69884103, compound

HRID 1059280Notes

Reaction equation

HRID 1059280 reaction equation
[CH2:1]=[O:2].[CH3:3][NH2:4].[CH3:5][CH:6]1[CH:10]([CH3:11])[CH2:9][C:8](=O)[CH2:7]1.[C:13](O)(=O)C>CO>[CH3:3][N:4]1[CH2:9][CH:8]2[C:1](=[O:2])[CH:10]([C@H:6]([CH3:5])[C@H:7]2[CH3:13])[CH2:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6329MethylamineHCID 1405543,4-Dimethylcyclopentanone

Product 1

HCID 69884103HCID 69884103, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 8 g of paraformaldehyde in methanol (100 ml) were added 10 ml of a 40% solution of methylamine in methanol, 7.7 ml of acetic acid and 10 g of 3,4-dimethylcyclopentanone and the resulting mixture was heated under reflux for 1.5 hours. After distilling off the solvent under reduced pressure, the residue was acidified by adding a dilute aqueous solution of hydrochloric acid and then was extracted with ethyl acetate. The aqueous layer was made basic with a dilute aqueous solution of sodium hydroxide and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Then the obtained residue was distilled under reduced pressure (70-75° C./1 mmHg) to thereby give 2.7 g of crude (6R*,7R*)-3,6,7-trimethyl-3-azabicyclo[3.2.1]octan-8-one as a pale yellow oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. distillationAfter distilling off the solvent under reduced pressure
  4. additionby adding a dilute aqueous solution of hydrochloric acid
  5. extractionwas extracted with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. distillationThen the obtained residue was distilled under reduced pressure (70-75° C./1 mmHg)

Sources & evidence

ORD record
ord-3f2cba01f6db450388027b5b2782a27f
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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