HCID 5138807, compound → HCID 131712299, compound

HRID 1278080Notes

Reaction equation

HRID 1278080 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:39]=[CH:38][C:31]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][NH:34]2)=[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:39]=[CH:38][C:31]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][NH:34]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 5138807HCID 5138807, compoundHCID 12362976dibenzoyl-L(+)tartaric acid

Product 1

HCID 131712299HCID 131712299, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Add a solution of 37.6 g of dibenzoyl-L-tartaric acid in 250 ml of acetone to 19.57 g of 2-(4-chlorobenzyl)pyrrolidine dissolved in 200 ml of acetone. Allow the resulting reaction mixture to stand for 12 hours and then filter off the precipitated crystals (25.8 g); [α]58920 =-84.7° (25 mg/ml in methanol). Recrystallize from 75 ml methanol/100 ml acetone to obtain 15.43 g of (-)-2-(4-chlorobenzyl)pyrrolidine dibenzoyl tartrate (m.p. 178° to 179°); [α]58920 =-88° (25 mg/ml in methanol). Stir 14.85 g of this salt with sodium hydroxide solution/diethyl ether until two clear phases form. Collect the ether phase and dry it over sodium sulfate. Thereafter, concentrate the dried ether phase to obtain the title compound as a colorless oil (5.0 g). Treat the colorless oil with methanol/ethereal hydrochloric acid to convert it into 4.83 g of the corresponding hydrochloride (m.p. 216° to 218°); [α]58920 =-31.4° (25 mg/ml in methanol).

Workup

  1. customthe resulting reaction mixture
  2. filtrationfilter off the precipitated crystals (25.8 g)
  3. custom[α]58920 =-84.7° (25 mg/ml in methanol)
  4. customRecrystallize from 75 ml methanol/100 ml acetone

Sources & evidence

ORD record
ord-9101f8124cb44ddfb358027320cb55da
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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