Reaktion #50945

ord-38ddfbcdcc454345a2a2f4edeccffcbc

Reaktionsgleichung

Cl
HCl
C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1
4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
O=S(Cl)Cl
thionyl chloride
→
C=C1CNN(C(=O)OCc2ccccc2)C1
desired product
Ausbeute 97.0%
C=C1CNN(C(=O)OCc2ccccc2)C1
4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester
Ausbeute 97.0%

Edukte

Cl
HCl
C=C1CN(C(=O)OCc2ccccc2)N(C(=O)OC(C)(C)C)C1
4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
O=S(Cl)Cl
thionyl chloride

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeConcentration of the reaction in vacuo
  2. 2
    Sonstigeaffords a yellow oil which
  3. 3
    Sonstigecrystallizes

Vorschrift

To a solution of crude 4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 8, (30 g) in methanol (300 ml.) is added thionyl chloride dropwise at 0° C. The reaction is warmed to room temperature and stirred an additional 18 hours. Concentration of the reaction in vacuo affords a yellow oil which crystallizes upon standing to provide 23 g (97% yield) of the desired product as the HCl salt.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06849627B2uspto-grants-2005_02