Isopropanol → HCID 67115019, compound

HRID 331097

Reaction equation

HRID 331097 reaction equation
C(C1(O)C[CH2:7][C@@H:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])C1)C=C.I([O-])(=O)(=O)=O.[Na+].[CH:26]([OH:29])([CH3:28])[CH3:27].[C:30]([O:33]CC)(=[O:32])[CH3:31]>O.[Ru](=O)=O>[CH2:12]([O:11][C:9]([CH:6]1[CH2:7][CH2:28][C:26]([CH2:31][C:30]([OH:33])=[O:32])([OH:29])[CH2:27]1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 86668862HCID 86668862, compound

Product 1

HCID 67115019HCID 67115019, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 16211523Ruthenium dioxide hydrateCatalyst

Procedure

To a solution of benzyl 3-allyl-3-hydroxycyclopentanecarboxylate (from step A, 150 mg, 0.576 mmol) in ethyl acetate (5 mL) was added ruthenium(IV) oxide hydrate (104 mg, 0.691 mmol) followed by 10% wt. aqueous sodium periodate solution (˜3 mL). The resulting mixture was stirred at room temperature for 4 hours. Isopropyl alcohol (3 mL) was added to quench the reaction. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to yield 2-(3-(benzyloxycarbonyl)-1-hydroxycyclopentyl)acetic acid (130 mg, 0.467 mmol, 81% yield) as an oil. It was used as such for the next step without further purification. MS (ESI+) m/z 301 (M+Na)+

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c69423bf614843c29e657b8be69a071f
Source dataset
uspto-grants-2014_11
Patent number
US08877749B2

Linked notes

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