Ammonium cerium (IV) nitrate → Acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester

HRID 2046214Notes

Reaction equation

HRID 2046214 reaction equation
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:30]2[CH2:35][CH2:34][N:33]3[N:36]=[C:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH:38]=[C:32]3[C:31]2=[O:44])=CC=1>O.C(#N)C>[O:44]=[C:31]1[NH:30][CH2:35][CH2:34][N:33]2[N:36]=[C:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH:38]=[C:32]12

Participants

5

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 67975764Acetic acid 5-(4-methoxy-benzyl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester

Product 1

HCID 67974158Acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl esterYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ammonium cerium (IV) nitrate (0.7 g, 1.29 mmol) in water (1.1 mL) was added to a stirred solution of acetic acid 5-(4-methoxy-benzyl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester (142 mg, 0.43 mmol) in ACN (4.3 mL). The mixture was stirred at room temperature for 30 minutes and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield acetic acid 4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester (56 mg, 62% yield) as a white solid.

Workup

  1. customthe solvents evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90)
  3. customThe desired fractions were collected
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0635435dcb23452e8f829673803a4dfc
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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