Trifluoroacetic acid → (R)-2-[2-(3-fluorophenyl)-ethyl]pyrrolidine

HRID 928086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928086
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)[CH:12]=[CH:13][CH:14]=1>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)[CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71006947tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylate2×

Produkt 1

HCID 86713377(R)-2-[2-(3-fluorophenyl)-ethyl]pyrrolidineAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl (R)-2-[2-(3-fluorophenyl)ethyl]-pyrrolidine-1-carboxylate (Intermediate 234, 0.55 g) in DCM (5 mL) and the mixture was stirred at room temperature for 1.5 hours. The mixture was evaporated to dryness and the residue was dissolved in a small amount of methanol and loaded onto a 20 g SCX-2 SPE cartridge, washed with methanol then eluted with 2M ammonia in methanol to give (R)-2-[2-(3-fluorophenyl)-ethyl]pyrrolidine (0.39 g).

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in a small amount of methanol
  3. washwashed with methanol
  4. washthen eluted with 2M ammonia in methanol

Quellen und Nachweise

ORD-Eintrag
ord-ab99dd8489684eb89307c6ddbd499d82
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

Notizen zur Reaktion

Wird geladen…