HCID 57771562, compound → HCID 57771436, compound

HRID 2070613Notes

Reaction equation

HRID 2070613 reaction equation
[CH2:1]1[C:3]2([CH2:9][CH2:8][CH2:7][CH2:6][C:5]([CH2:10][OH:11])=[CH:4]2)[CH2:2]1.[H][H]>C(O)C.[Pt]=O>[CH2:1]1[C:3]2([CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([CH2:10][OH:11])[CH2:4]2)[CH2:2]1

Participants

5

Reactant 2

HCID 57771562HCID 57771562, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57771436HCID 57771436, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of spiro[2.6]non-4-en-5-yl-methanol (170 mg) obtained in Step 4 in ethanol (3.4 mL) was added platinum oxide (35 mg), followed by stirring the reaction mixture at room temperature under normal pressure in an atmosphere of hydrogen for 2 hours. Then, the reaction mixture was filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:7) to give spiro[2.6]non-5-yl-methanol (164 mg).

Workup

  1. filtrationThen, the reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:7)

Sources & evidence

ORD record
ord-6ba77306a5b246229dcefe2c68bb6200
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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