3-Aminopyrrolidine → (3R)-3-Aminopyrrolidine D(-)-tartrate

HRID 2165252Notes

Reaction equation

HRID 2165252 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[NH2:11][CH:12]1[CH2:16][CH2:15][NH:14][CH2:13]1>O.CO>[C:6]([C@H:4]([C@@H:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[NH2:11][C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1

Participants

5

Reactant 2

HCID 1644013-AminopyrrolidineHCID 439655D-Tartaric acid

Product 1

HCID 15107948(3R)-3-Aminopyrrolidine D(-)-tartrateYield 25.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

D(-)-tartaric acid (17 g) is dissolved in a mixture of water (30 ml) and methanol (120 ml), and to the solution is gradually added (3RS)-3-aminopyrrolidine (19 g), and the mixture is stirred. When exothermic reaction is finished, methanol (60 ml) is added to the mixture, and the mixture is allowed to stand at 0°-2° C. overnight. The precipitated crude (3R)-3-aminopyrrolidine D(-)-tartrate (20.6 g) is taken by filtration. This product is recrystallized from a mixture of methanol-water (2:3) four times to give (3R)-3-aminopyrrolidine D(-)-tartrate (6.8 g).

Workup

  1. customWhen exothermic reaction
  2. customThe precipitated crude (3R)-3-aminopyrrolidine D(-)-tartrate (20.6 g)
  3. filtrationis taken by filtration
  4. customThis product is recrystallized from a mixture of methanol-water (2:3) four times

Sources & evidence

ORD record
ord-14c62699e9f84ba4b7d688d56285e52f
Source dataset
uspto-grants-1990_07
Patent number
US04939256

Reaction notes

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