2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine → 2-(1,4-Dioxaspiro[4.5]decan-8-yl)pyridine

HRID 1383777Notes

Reaction equation

HRID 1383777 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>C(OCC)(=O)C.[Pd]>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 211876502-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine

Product 1

HCID 211876632-(1,4-Dioxaspiro[4.5]decan-8-yl)pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 14.6 g (67.19 mmol) of 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine in ethyl acetate (400 mL) was added 4.6 g of 10% palladium on carbon catalyst. The resulting suspension was then hydrogenated at ambient temperature and atmospheric pressure until all the starting material was consumed (10.5 hr). The reaction mixture was filtered through celite and the filtrate was concentrated to give the product as an oily solid.

Workup

  1. customwas then hydrogenated at ambient temperature
  2. customatmospheric pressure until all the starting material was consumed (10.5 hr)
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-365e63e73c6841f0a37f97f24c639be6
Source dataset
uspto-grants-2001_07
Patent number
US06255315B1

Reaction notes

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