Trifluoroacetic acid → (R)-1-(3-Trifluoromethylpyridin-2-yl)pyrrolidin-3-ylamine

HRID 490292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490292
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:21][C:19]([F:20])([F:22])[C:18]1[C:13]([N:10]2[CH2:11][CH2:12][C@@H:8]([NH2:7])[CH2:9]2)=[N:14][CH:15]=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67001808[(R)-1-(3-Trifluoromethylpyridin-2-yl)pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 68801104(R)-1-(3-Trifluoromethylpyridin-2-yl)pyrrolidin-3-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of D1 (11.5 g, 0.04 mol) in DCM (80 ml) was cooled (ice-bath) and TFA (excess, 50ml) was added. Reaction was warmed to ambient temperature, stirred for 3 h and partitioned between ethyl acetate and aqueous sodium hydroxide. The organic phase was separated, dried (MgSO4) and filtered. Removal of solvent under reduced pressure afforded the crude product as a yellow oil. Bulb to bulb distillation under reduced pressure initially afforded the product as a oil which crystallised on standing.

Aufarbeitung

  1. additionwas added
  2. customReaction
  3. custompartitioned between ethyl acetate and aqueous sodium hydroxide
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customRemoval of solvent under reduced pressure
  8. customafforded the crude product as a yellow oil
  9. distillationBulb to bulb distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0b09710278c5484d9aeca4615102ac59
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528151B2

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