Tetrabutylammonium Fluoride → (S)-tert-Butyl 2-(fluoromethyl)pyrrolidine-1-carboxylate

HRID 494884

Reaktionsgleichung

Reaktionsgleichung von HRID 494884
CS(O[CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[F-:19].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:19][CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 10039261tert-butyl (2S)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate

Produkt 1

HCID 86586409(S)-tert-Butyl 2-(fluoromethyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The product from Example 164A (7 g) in 100 mL of THF and tetrabutylammonium fluoride (42 mL of a 1M solution in THF) was heated at reflux for 17 hours, cooled, concentrated to dryness, diluted with 125 mL of ethyl acetate, washed with 5% aqueous NaHCO3, brine, dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure to provide an oil. The oil was distilled in vacuo (50° C., 1.2 torr) to give 4.9 g of the title compound as a colorless oil.

Aufarbeitung

  1. temperatureat reflux for 17 hours
  2. temperaturecooled
  3. concentrationconcentrated to dryness
  4. additiondiluted with 125 mL of ethyl acetate
  5. washwashed with 5% aqueous NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customto provide an oil
  10. distillationThe oil was distilled in vacuo (50° C., 1.2 torr)

Quellen und Nachweise

ORD-Eintrag
ord-3632172ee19647fa92f7735f0b043926
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538138B2

Verknüpfte Notizen

Wird geladen…