HCID 11845250, compound → HCID 11847134, compound

HRID 1158892Notes

Reaction equation

HRID 1158892 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]3[N:18]=[C:19]([CH2:21][OH:22])[CH:20]=[C:14]3[CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]>O=[Mn]=O.C(Cl)(Cl)Cl.CO>[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]3[N:18]=[C:19]([CH:21]=[O:22])[CH:20]=[C:14]3[CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 11845250HCID 11845250, compound

Product 1

HCID 11847134HCID 11847134, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21584188Chloroform methanolSolvent

Procedure

MnO2 (activated) (84.2 g) was added to the CHCl3-MeOH (95:5, 253 mL) solution of 2-hydroxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazine-5-carboxylic acid 4-nitrobenzyl ester (8.42 g), and the mixture was refluxed for 1 h under a nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite. Silica-gel (20 g) was added to the filtrate and the solvent was removed under reduced pressure to give the silica-gel coating with crude reactant. The above silica-gel was adsorbed to silica-gel column chromatography and the column was eluted with CHCl3-MeOH (49/1 to 19/1). The titled compound was obtained as yellow crystals (2.82 g, 34%).

Workup

  1. temperaturethe mixture was refluxed for 1 h under a nitrogen atmosphere
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. additionSilica-gel (20 g) was added to the filtrate
  4. customthe solvent was removed under reduced pressure
  5. customto give the silica-gel coating with crude reactant
  6. washthe column was eluted with CHCl3-MeOH (49/1 to 19/1)

Sources & evidence

ORD record
ord-e7ee7bd354054811aa814a0b432c16b0
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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