L-Tartaric acid → HCID 86753194, compound

HRID 398845Notes

Reaction equation

HRID 398845 reaction equation
[NH2:1][C@H:2]1[C@H:6]([O:7][CH3:8])[CH2:5][N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]1.[C:16]([OH:25])(=[O:24])[C@@H:17]([C@H:19]([C:21]([OH:23])=[O:22])[OH:20])[OH:18]>CO>[C:21]([C@@H:19]([C@H:17]([C:16]([OH:25])=[O:24])[OH:18])[OH:20])([OH:23])=[O:22].[NH2:1][C@H:2]1[C@H:6]([O:7][CH3:8])[CH2:5][N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 15069967(3R,4R)-1-Benzyl-4-methoxypyrrolidin-3-amine

Product 1

HCID 86753194HCID 86753194, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trans-3-amino-1-benzyl-4-methoxypyrrolidine (racemic; 22.4 g) disclosed in Japanese Laid-open Patent Publication No. 69474/1990 and 19.6 g of L-tartaric acid were dissolved in methanol (350 ml), and the resulting solution was left still at room temperature for 7 hours. Precipitated L-tartrate was taken by filtration, and then, was subjected to recrystallization with methanol and water, and thus, there was obtained trans-3-amino-1-benzyl-4-methoxypyrrolidine L-tartrate (14.1 g) having the following physical properties. Then, all the mother liquors were put together, and the solvent was distilled off under reduced pressure, and then, a saturated brine was added, and, subsequently, potassium carbonate was added so that the obtained mixture might become basic. Then, the mixture was extracted with ethyl acetate. The obtained extract was washed with saturated brine, and was then dried over anhydrous sodium sulfate, and solvent was distilled off under reduced pressure. The resultant residue and D-tartaric acid (6.73 g) were dissolved in methanol (180 ml), and the obtained solution was left still at room temperature for 7 hours. Precipitated D-tartrate was taken by filtration, and was then subjected to recrystallization with methanol and water, and thus, there was obtained trans-3-amino-1-benzyl-4-methoxypyrrolidine D-tartrate (9.9 g) having the following physical properties.

Workup

  1. filtrationPrecipitated L-tartrate was taken by filtration
  2. customwas subjected to recrystallization with methanol and water

Sources & evidence

ORD record
ord-76ff48eebb8f4ac99f351c8730b60e33
Source dataset
uspto-grants-1998_10
Patent number
US05817669

Reaction notes

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