Sodium periodate → 5-Oxo-4-azaspiro[2.4]heptane-7-carbaldehyde

HRID 595260Notes

Reaction equation

HRID 595260 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH:7]([CH:9]1[C:13]2([CH2:15][CH2:14]2)[NH:12][C:11](=[O:16])[CH2:10]1)=C>CO.O.[Os](=O)(=O)(=O)=O>[O:16]=[C:11]1[CH2:10][CH:9]([CH:7]=[O:2])[C:13]2([CH2:15][CH2:14]2)[NH:12]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 916184657-Ethenyl-4-azaspiro[2.4]heptan-5-one

Product 1

HCID 916185615-Oxo-4-azaspiro[2.4]heptane-7-carbaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Osmium tetroxide (55 mg, 0.22 mmol) and sodium periodate (1.4 g, 6.6 mmol) were added in portions to a solution of 7-ethenyl-4-azaspiro[2.4]heptan-5-one (0.50 g, 3.3 mmol) in methanol (8 mL) and water (12 mL) at room temperature. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered and the filtrate was dried under reduced pressure to afford 5-oxo-4-azaspiro[2.4]heptane-7-carbaldehyde. The material was used in the next step without purification. MS ESI calc'd. for C7H10NO2 [M+H]+ 140. found 140.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was dried under reduced pressure

Sources & evidence

ORD record
ord-670f38027df848a39309ab83a83fc45f
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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