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 220158Notes

Reaction equation

HRID 220158 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-e7fdb285f10743ae95949d2a19412180
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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