Reaction #2275727

ord-9ab9905baa1c470ca236d29b40e48295

Reaction equation

O=c1ccccn1C1CCC2(CC1)OCCO2
1-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-pyridin-2-one
Cl
HCl
O=C([O-])O.[Na+]
sodium bicarbonate
O=C1CCC(n2ccccc2=O)CC1
title compound
O=C1CCC(n2ccccc2=O)CC1
1-(4-Oxo-cyclohexyl)-1H-pyridin-2-one

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was removed in vacuo and residue
  2. 2
    Otherpartitioned between ethyl acetate and water
  3. 3
    WashThe organic layer was washed with brine
  4. 4
    Dryingdried over anhydrous Na2SO4
  5. 5
    Filtrationfiltered
  6. 6
    Concentrationconcentrated

Procedure

A solution of 1-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-pyridin-2-one (as prepared in the previous step, ˜300 mg, 1.28 mmol)) in acetone (10 mL) was treated with 1N HCl (2 mL) at room temperature for 4 hours. The reaction was worked up with saturated sodium bicarbonate to adjust the pH to neutral. The solvent was removed in vacuo and residue partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated to afford the title compound as white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08324186B2uspto-grants-2012_12