dibenzoyl-L(+)tartaric acid → (+)-2-(4-Chlorobenzyl)-1-methylpyrrolidine dibenzoyl tartrate

HRID 1278067Notes

Reaction equation

HRID 1278067 reaction equation
[C:1]([C@@:9]([C:24]([OH:26])=[O:25])([OH:23])[C@@:10]([C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:14])[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:27][C:28]1[CH:40]=[CH:39][C:31]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][N:34]2[CH3:38])=[CH:30][CH:29]=1>CC(C)=O>[C:15]([C:10]([C:11]([OH:13])=[O:12])([OH:14])[C:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:23])[C:24]([OH:26])=[O:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl:27][C:28]1[CH:40]=[CH:39][C:31]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][N:34]2[CH3:38])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 12362976dibenzoyl-L(+)tartaric acidHCID 234525052-[(4-Chlorophenyl)methyl]-1-methylpyrrolidine

Product 1

HCID 131712298(+)-2-(4-Chlorobenzyl)-1-methylpyrrolidine dibenzoyl tartrateYield 24.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Add a solution of 27 g of dibenzoyl-L-tartaric acid in 200 ml of acetone to 15 g of 2-(4-chlorobenzyl)-1-methylpyrrolidine dissolved in 100 ml of acetone. Allow the resulting mixture to stand for 6 hours at room temperature and for 4 days at 0°. Filter off the precipitated crystals (8.5 g). Concentrate the filtrate somewhat and then allow the mixture to stand for a further 12 hours at 0°. Collect the further-precipitated crystals (4.53 g). Recrystallize the collected crystalline products from 100 ml of acetone and filter to obtain a total yield of 9.9 g of (+)-2-(4-chlorobenzyl)-1-methylpyrrolidine dibenzoyl tartrate, m.p. 117° to 120°, [α]58920 =-64° (25 mg/ml in methanol). Shake 9.4 g of this salt with diethyl ether/sodium hydroxide solution until solution is complete. Dry the ether phase, evaporate off the solvent and distill the residue to obtain 2.73 g of the base, the title compound, b.p. 70° at 0.005 mm of Hg, [α]58920 =+78.9° (25 mg/ml in methanol).

Workup

  1. filtrationFilter off the precipitated crystals (8.5 g)
  2. concentrationConcentrate the filtrate somewhat
  3. waitto stand for a further 12 hours at 0°
  4. customCollect the further-precipitated crystals (4.53 g)
  5. customRecrystallize the collected crystalline products from 100 ml of acetone
  6. filtrationfilter

Sources & evidence

ORD record
ord-545daa1a3b8746cdbd2498a49a4dc9c7
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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