Methyl 6-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)nicotinate → Methyl 6-(1,4-dioxaspiro[4,5]decan-8-yl)nicotinate

HRID 2042742Notes

Reaction equation

HRID 2042742 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H][H]>CO.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 69059497Methyl 6-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)nicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 69060042Methyl 6-(1,4-dioxaspiro[4,5]decan-8-yl)nicotinate

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium hydroxide on carbon (1 g, 20 wt % Pd) was added to a solution of Example 93A (2.66 g, 9.66 mmol) in methanol (40 mL) and ethyl acetate (10 mL). The mixture was placed under vacuum and filled with hydrogen (balloon) and allowed to stir for 3 hours before it was filtered through a pad of Celite using methanol to rinse. The solvent was evaporated and the product was dissolved in dichloromethane and dried over Na2SO4. After filtration and concentration, the title compound was isolated as a slightly yellow solid and used in the following step without further purification.

Workup

  1. filtrationwas filtered through a pad of Celite
  2. washto rinse
  3. customThe solvent was evaporated
  4. dissolutionthe product was dissolved in dichloromethane
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-5bf52f44ea554f6cbfc9744a610b0de2
Source dataset
uspto-grants-2013_11
Patent number
US08586594B2

Reaction notes

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