Methyl 6-oxospiro[4.5]decane-7-carboxylate → 6-Hydroxy-spiro[4.5]decane-7-carboxylic acid methyl ester

HRID 2070547Notes

Reaction equation

HRID 2070547 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[C:6]1=[O:15])=[O:4].[H][H]>CO.[Pt]=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]1[OH:15])=[O:4]

Participants

5

Reactant 2

HCID 57429459Methyl 6-oxospiro[4.5]decane-7-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 577715366-Hydroxy-spiro[4.5]decane-7-carboxylic acid methyl esterYield 100.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-oxo-spiro[4.5]decane-7-carboxylic acid methyl ester (9.99 g) obtained in Step 2 in methanol (200 mL) was added platinum oxide (0.2 g) in an atmosphere of hydrogen (<0.3 Mpa) at room temperature overnight. Then, the reaction mixture was filtered through Celite and the filtrate was concentrated. After adding ethyl acetate (30 mL) and n-hexane (30 mL) to the residue, the resulting insolubles were filtered off. The filtrate was concentrated and then dried in vacuo to give 6-hydroxy-spiro[4.5]decane-7-carboxylic acid methyl ester (10.11 g).

Workup

  1. filtrationThen, the reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. additionAfter adding ethyl acetate (30 mL) and n-hexane (30 mL) to the residue
  4. filtrationthe resulting insolubles were filtered off
  5. concentrationThe filtrate was concentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-47e431cb42c5414baacc9a611d95acb9
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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