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1-Chloroethyl chloroformate → methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochloride

HRID 2047439
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2047439
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[C@@H:10]([C:21]([O:23][CH3:24])=[O:22])[CH2:9]1)C1C=CC=CC=1.CC(Cl)OC(Cl)=O>C(#N)C>[ClH:19].[Cl:20][C:15]1[CH:14]=[C:13]([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H:10]2[C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][C:16]=1[Cl:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 67232866methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

Produkt 1

HCID 67232915methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochlorideAusbeute 188,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of the compound (33.4 g) obtained in step 2 in acetonitrile (250 mL) was added ACE-Cl (13.9 g) at room temperature, and the mixture was stirred at 90° C. for 2 hr. The reaction solution was cooled, and the solvent was evaporated under reduced pressure. To the residue was added methanol (250 mL), and the mixture was stirred at 80° C. for 2 hr. The reaction solution was cooled, the solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate/IPE to give methyl (3R*,4S*)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate monohydrochloride (26.9 g, 98%) as a pale-yellow powder.

Aufarbeitung

  1. temperatureThe reaction solution was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the residue was added methanol (250 mL)
  4. stirringthe mixture was stirred at 80° C. for 2 hr
  5. temperatureThe reaction solution was cooled
  6. customthe solvent was evaporated under reduced pressure
  7. washthe residue was washed with ethyl acetate/IPE

Quellen und Nachweise

ORD-Eintrag
ord-07ae5e7febea407397f4f809797c8df5
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592454B2

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