2-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-pyridin-3-ol → 2-(1,4-Dioxa-spiro[4.5]dec-8-yl)-pyridin-3-ol

HRID 1896800Notes

Reaction equation

HRID 1896800 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>CO.[OH-].[Pd+2].[OH-]>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 585625152-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-pyridin-3-ol

Product 1

HCID 585628682-(1,4-Dioxa-spiro[4.5]dec-8-yl)-pyridin-3-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-pyridin-3-ol (1.3 g, 5.573 mmol) in methanol (60 mL) added to palladium (II) hydroxide (330 mg, 0.62 mmol) in a Parr bottle under argon. The reaction mixture was degassed with argon, evacuated and backfilled with hydrogen then shaken under 50 psi the gas at ambient temperature for 24 hours. After depressurizing and bubbling with argon, the reaction mixture was filtered through Celite 521, washing the filter with MeOH, and filtrate evaporated in vacuo giving a white solid.

Workup

  1. customThe reaction mixture was degassed with argon
  2. customevacuated
  3. custombubbling with argon
  4. filtrationthe reaction mixture was filtered through Celite 521
  5. washwashing the
  6. filtrationfilter with MeOH, and filtrate
  7. customevaporated in vacuo
  8. customgiving a white solid

Sources & evidence

ORD record
ord-a3610658743b44499f9406a79442c075
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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