Sodium Sulfate → HCID 59187100, compound

HRID 1921150Notes

Reaction equation

HRID 1921150 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2([CH2:16][CH2:17][C:18](OCC)=[O:19])[CH2:14][CH2:13][C:12](=O)[NH:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2([CH2:16][CH2:17][CH2:18][OH:19])[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67493350HCID 67493350, compound

Product 1

HCID 59187100HCID 59187100, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.321 g (7.58 mmol) of ethyl 3-[3-(6-methoxypyridin-3-yl)-6-oxopiperidin-3-yl]propanoate obtained in stage 1.2, in solution in 128 ml of anhydrous tetrahydrofuran, are introduced at ambient temperature into a 250 ml round-bottomed flask. 2.876 g (75.8 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 1.80 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-fbb6b9c19922496fa8722ab53b8546b2
Source dataset
uspto-grants-2012_05
Patent number
US08173669B2

Reaction notes

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