HCID 58537899, compound → HCID 58537907, compound

HRID 1473756Notes

Reaction equation

HRID 1473756 reaction equation
C([O:8][C:9]1[C:13]2([CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]2)[N:12]([CH3:21])[C:11](=[O:22])[C:10]=1[C:23]1[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=1[CH3:31])C1C=CC=CC=1>CO.O.[Pd]>[OH:8][C:9]1[C:13]2([CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]2)[N:12]([CH3:21])[C:11](=[O:22])[C:10]=1[C:23]1[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=1[CH3:31]

Participants

5

Reactant 1

HCID 58537899HCID 58537899, compound

Product 1

HCID 58537907HCID 58537907, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-benzyloxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (22.6 g, 53.7 mmol) in methanol (226 ml) and water (22.6 ml) in a Parr shaker type hydrogenator was added 5% Pd/C (22.6 g). After hydrogenation under 4 bars H2 at 36° C. for 22 hours, the reaction mixture was filtered and concentrated. The residue was diluted with ethyl acetate and extracted with saturated aqueous sodium carbonate under ice cooling. The organic layer was discarded, the aqueous alkaline phase acidified with cooling to pH 5-6 with an aqueous HCl solution and thoroughly extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. Yield: 13.0 g of 4-hydroxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2.2) as a solid, mp 239-241° C. The spectral data were identical to those described above under preparation example 1, step 1.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate
  4. extractionextracted with saturated aqueous sodium carbonate under ice cooling
  5. temperaturewith cooling to pH 5-6 with an aqueous HCl solution
  6. extractionthoroughly extracted with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customthose described above under preparation example 1, step 1

Sources & evidence

ORD record
ord-bdf4e600c23d4b569c4e2cf973ba6dae
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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