Hydrochloric Acid → (S)-3-methanesulfonyloxypyrrolidine hydrochloride

HRID 612850

Reaktionsgleichung

Reaktionsgleichung von HRID 612850
C([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:9]1)C1C=CC=CC=1.[ClH:18].[H][H]>[C].[Pd].C(O)C>[ClH:18].[CH3:17][S:14]([O:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)(=[O:16])=[O:15]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86754980(S)-3-methanesulfonyloxypyrrolidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixed solution obtained by mixing 2.3 g of 100% pure (S)-1-benzyl-3-methanesulfonyloxypyrrolidine with 3.0 ml of ethanol and adding dropwise 1.00 ml of 35% aqueous hydrochloric acid thereto with cooling on an ice-water bath was charged, together with 300 mg of moist 5% palladium-carbon (water content 52% by weight), into an autoclave, hydrogen was introduced thereinto and the autoclave was heated to raise the temperature to 60 and the pressure to 203 kPa, and the reaction was allowed to proceed for 4 hours. Hydrogen absorption came to an end in 3.2 hours after the start of hydrogen introduction. After completion of the reaction, the reaction mixture was cooled to room temperature and depressurized. The reaction mixture was taken out, the catalyst was filtered off, and the filtrate obtained was concentrated under reduced pressure and further dried under vacuum to give 2.4 g (yield: 84 mole percent) of (S)-3-methanesulfonyloxypyrrolidine hydrochloride.

Aufarbeitung

  1. customA mixed solution obtained
  2. temperaturewith cooling on an ice-water bath
  3. additionwas introduced
  4. temperaturethe autoclave was heated
  5. temperatureto raise the temperature to 60
  6. customHydrogen absorption
  7. waitcame to an end in 3.2 hours
  8. customAfter completion of the reaction
  9. filtrationthe catalyst was filtered off
  10. customthe filtrate obtained
  11. concentrationwas concentrated under reduced pressure
  12. customfurther dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cd11b9db3fbe41d1bb5ca0c8b95ade54
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005119

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