HCID 68707416, compound → HCID 22224545, compound

HRID 1744990Notes

Reaction equation

HRID 1744990 reaction equation
[OH:1][CH2:2][C:3]1[CH:19]=[C:6]2[O:7][C:8]3[CH2:9][N:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:12][C:13]=3[N:5]2[N:4]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:19]=[C:6]2[O:7][C:8]3[CH2:9][N:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:12][C:13]=3[N:5]2[N:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 68707416HCID 68707416, compound

Product 1

HCID 22224545HCID 22224545, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To the stirred solution of ethyl 2-(hydroxymethyl)-7,8-dihydropyrazolo [5′, 1′:2,3][1,3]oxazolo[5,4-c]pyridine-6(5H)-carboxylate (1.76 g, 6.6 mmol) in 60 ml of CHCl3 was added 10 g of MnO2. Th suspension was refluxed for 1.5 hour under a nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated to give yellow solid. The product was purified by chromatography. 1.43 g of the product was obtained (82%); M.pt: 97–99° C. (M+H) 264.

Workup

  1. temperatureTh suspension was refluxed for 1.5 hour under a nitrogen atmosphere
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. customto give yellow solid
  5. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-1cc38c9cbf4b43fd9b485b17a080cf47
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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