Sodium Bicarbonate → (2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidine

HRID 650387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650387
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[F:24][C:21]([F:22])([F:23])[C:18]1[CH:17]=[CH:16][C:15]([S:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 69338860N-tert-butyloxycarbonyl-(2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidine

Produkt 1

HCID 57133071(2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidineAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 2.55 g of N-tert-butyloxycarbonyl-(2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidine in 5.64 ml of trifluoroacetic acid is stirred for 1 hour at 0° C. and then for 3.5 hours at room temperature. The reaction mixture is poured onto 10% sodium bicarbonate solution, extracted with ethyl acetate, washed twice with 2 M hydrochloric acid, the water phase is extracted with ether, made basic with sodium bicarbonate, extracted three times with ethyl acetate, washed with common salt solution, dried on sodium sulfate and concentrated by evaporation. 557 mg of (2S)-2-(4-trifluoromethylphenylthio-methyl)-pyrrolidine is obtained.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed twice with 2 M hydrochloric acid
  3. extractionthe water phase is extracted with ether
  4. extractionextracted three times with ethyl acetate
  5. washwashed with common salt solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-fec040b384d24d21b03cf1e807ccb037
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271403B1

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