Dimethyl 3-oxoglutarate → HCID 178499534, compound

HRID 1253440Notes

Reaction equation

HRID 1253440 reaction equation
Cl.Cl.[CH2:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([N:14](C(C)C)CC)(C)C.O=[C:21]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:22][C:23](OC)=[O:24]>C1(C)C=CC=CC=1>[CH2:3]([N:10]1[C:23]([OH:24])=[CH:22][C:21]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[N:14]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 74591Dimethyl 3-oxoglutarateHCID 81531DiisopropylethylamineHCID 19083749HCID 19083749, compound

Product 1

HCID 178499534HCID 178499534, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of benzylamine dihydrochloride (1.000 g, 5.126 mmol, 1 equiv.) in anhydrous toluene (25 ml) were added successively diisopropylethylamine (1.32 ml, 10.252 mmol, 2 equiv) and dimethyl 3-oxopentanedioate (0.893 g, 5.126 mmol, 1 equiv.). The resulting mixture was heated at reflux for 18 h before being concentrated in vacuo. The resulting brown oil was purified by flash chromatography over SiO2 (CH2Cl2:MeOH, 97:3). 0.810 g of pure methyl (1-benzyl-5-hydroxy-1H-pyrazol-3-yl)acetate was obtained as a white solid. Yield 64%. MS (ESI+): 247.1; MS (ESI−): 245.1.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationbefore being concentrated in vacuo
  4. customThe resulting brown oil was purified by flash chromatography over SiO2 (CH2Cl2:MeOH, 97:3)

Sources & evidence

ORD record
ord-1eb518f4a2944255b708f35cfd0d8c29
Source dataset
uspto-grants-2013_06
Patent number
US08455486B2

Reaction notes

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