L-Tartaric acid → HCID 86744075, compound

HRID 1073317Notes

Reaction equation

HRID 1073317 reaction equation
[C:1]([C@H:4]([C@@H:6]([C:8]([OH:10])=[O:9])[OH:7])[OH:5])([OH:3])=[O:2].[NH2:11][C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1.C(O)(=O)[C@@H]([C@H](C(O)=O)O)O>O>[C:1]([C@@H:4]([C@H:6]([C:8]([OH:10])=[O:9])[OH:7])[OH:5])([OH:3])=[O:2].[NH2:11][C@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 15107948(3R)-3-Aminopyrrolidine D(-)-tartrate

Product 1

HCID 86744075HCID 86744075, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To the filtrate obtained in the above crude (3R)-3-aminopyrrolidine D(-)-tartrate is added a solution of L(+)-tartaric acid (25 g) in water (50 ml), and the precipitated crystals are separated by filtration. The product is dissolved in a 20% aqueous sodium hydroxide solution (50 ml) and thereto is added acetone (300 ml), and the precipitated crystals are removed by filtration. To the filtrate is added a solution of L(+)-tartaric acid (20 g) in water (40 ml). The precipitated crystals are separated by filtration and dissolved in water (30 ml), and thereto is added sodium hydroxide (300 g). The mixture is extracted with ether (300 ml) three times. Ether is distilled off under reduced pressure, and to the residue is added a solution of L(+)-tartaric acid (5.5 g) in water (25 ml), and the mixture is heated at 80° C. To the mixture is added methanol (40 ml), and the mixture is gradually cooled till room temperature. The precipitated crystals are separated by filtration and recrystallized from a mixed solvent of methanol-water (1:1) to give (3S)-3-aminopyrrolidine L(+)tartrate (5.0 g).

Workup

  1. customthe precipitated crystals are separated by filtration
  2. dissolutionThe product is dissolved in a 20% aqueous sodium hydroxide solution (50 ml)
  3. additionis added acetone (300 ml)
  4. customthe precipitated crystals are removed by filtration
  5. additionTo the filtrate is added a solution of L(+)-tartaric acid (20 g) in water (40 ml)
  6. customThe precipitated crystals are separated by filtration
  7. dissolutiondissolved in water (30 ml)
  8. additionis added sodium hydroxide (300 g)
  9. extractionThe mixture is extracted with ether (300 ml) three times
  10. distillationEther is distilled off under reduced pressure
  11. additionto the residue is added a solution of L(+)-tartaric acid (5.5 g) in water (25 ml)
  12. additionTo the mixture is added methanol (40 ml)
  13. temperaturethe mixture is gradually cooled till room temperature
  14. customThe precipitated crystals are separated by filtration
  15. customrecrystallized from a mixed solvent of methanol-water (1:1)

Sources & evidence

ORD record
ord-547b994f032d4200a72ebb323c55d1b8
Source dataset
uspto-grants-1990_11
Patent number
US04968800

Reaction notes

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