HCID 15338089, compound → HCID 23355438, compound

HRID 234721Notes

Reaction equation

HRID 234721 reaction equation
[CH:1]1([N:6]2[C:10]3[C:11](=O)[N:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:13][C:9]=3[C:8]([CH2:21][CH3:22])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH:1]1([N:6]2[C:10]3[CH2:11][N:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:13][C:9]=3[C:8]([CH2:21][CH3:22])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 15338089HCID 15338089, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 23355438HCID 23355438, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-cyclopentyl-3-ethyl-6-oxo-5-phenyl-4,6-dihydro-1H-pyrazolo[3,4-c]pyrrole (0.17 g, 0.58 mmole) in anhydrous ether (15 ml) was added lithium aluminum hydride (0.17 g, 4.6 mmole). The majority of the ether (12-13 ml) was then removed by distillation, and the remaining mixture diluted with toluene (25 ml) and heated to reflux over 24 hours. The mixture was cooled to 0° C. and cautiously treated with ice. The resulting mixture was filtered through celite, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was chromatographed on a silica column using 1:9 ethyl acetate/hexane as eluent to give 100 mg of a colorless oil. 1H NMR (250 MHz, CDCl3) δ1.26 (t, J=7.6 Hz, 3H), 1.65-2.25 (m, 8H), 2.67 (q, J=7.6 Hz, 2H), 4.35 (s, 2H), 4.45 (s, 2H), 4.53 (pentet, J=7.5 Hz, 1H), 6.61 (d, J=8.1 Hz, 2H), 6.74 (t, J=7.4 Hz, 1H), 7.29 (dd, J=7.5 and 8.4 Hz 2H); MS m/z 282.

Workup

  1. customThe majority of the ether (12-13 ml) was then removed by distillation
  2. additionthe remaining mixture diluted with toluene (25 ml)
  3. temperatureheated
  4. temperatureto reflux over 24 hours
  5. additioncautiously treated with ice
  6. filtrationThe resulting mixture was filtered through celite
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude residue was chromatographed on a silica column

Sources & evidence

ORD record
ord-5b9c6f7fe9124ceea467f8521c6f0015
Source dataset
uspto-grants-1997_01
Patent number
US05596013

Reaction notes

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