Sodium Sulfate → HCID 59187098, compound

HRID 1921155Notes

Reaction equation

HRID 1921155 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([C:12]2[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:10][C:9](=O)[NH:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:19][O:18][C:15]1[N:14]=[CH:13][C:12]([C:6]2([CH2:5][CH2:4][OH:3])[CH2:10][CH2:9][NH:8][CH2:7]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86638967HCID 86638967, compound

Product 1

HCID 59187098HCID 59187098, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.50 g (5.39 mmol) of ethyl[3-(6-methoxypyridin-3-yl)-5-oxopyrrolidin-3-yl]acetate obtained in stage 4.2, in solution in 90 ml of anhydrous tetrahydrofuran, are introduced into a 250 ml round-bottomed flask at ambient temperature. 2.046 g (53.90 mmol) of lithium aluminum hydride are added portionwise and the resulting mixture is subsequently stirred at ambient temperature for 3 hours. The mixture is subsequently hydrolyzed with a saturated aqueous sodium sulfate solution, filtered through celite and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, elution being carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 90/10/1, to provide 0.41 g of the desired compound in the form of a yellow wax.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue obtained
  4. customis purified by chromatography on a column of silica gel, elution
  5. additionbeing carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 90/10/1

Sources & evidence

ORD record
ord-f5a881a8566f4098889fdafd4d121d5b
Source dataset
uspto-grants-2012_05
Patent number
US08173669B2

Reaction notes

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