HCID 67439261, compound → 1-methyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

HRID 1664796Notes

Reaction equation

HRID 1664796 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:11][CH2:10][N:9](C(OCC3C=CC=CC=3)=O)[CH2:8][CH2:7]2)[C:5](=[O:22])[NH:4][C:3]1=[O:23]>C(O)C.[Pd]>[CH3:1][N:2]1[C:6]2([CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[C:5](=[O:22])[NH:4][C:3]1=[O:23]

Participants

4

Reactant 1

HCID 67439261HCID 67439261, compound

Product 1

HCID 2720021-methyl-1,3,8-triazaspiro[4.5]decane-2,4-dioneYield 66.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium (10% on carbon; 1.0 g) was added to a solution of benzyl 1-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (7.82 g, 24.6 mmol) in ethanol (100 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 2 h, methanol (50 mL) was added to the reaction mixture and the mixture was continued to be stirred under hydrogen (1 atm). After 4 days, the mixture was filtered through celite, washed with acetone and concentrated. The mixture was diluted in acetic acid (50 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 2 h, the mixture was filtered through celite, and concentrated to give the acetate salt of the title compound (2.98 g). MS 184.1 (M+1).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. additionmethanol (50 mL) was added to the reaction mixture
  5. waitAfter 4 days
  6. filtrationthe mixture was filtered through celite
  7. washwashed with acetone
  8. concentrationconcentrated
  9. additionThe mixture was diluted in acetic acid (50 mL)
  10. customThe reaction vessel was evacuated
  11. additionback-filled with nitrogen (3×)
  12. additionback-filled with hydrogen (1 atm)
  13. waitAfter 2 h
  14. filtrationthe mixture was filtered through celite
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-efe9ab24a9e94a77b8b5ea65a5bc0c6b
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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