Sodium Bicarbonate → tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 2401281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401281
O[CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].COCCN(S(F)(F)[F:29])CCOC.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:29][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 10879805Tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Produkt 1

HCID 86705185tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (3.05 g) in chloroform (40 mL) was cooled in a dry ice-acetone bath, bis(2-methoxyethyl)aminosulfur trifluoride (2.77 mL) was added thereto, and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, and the organic layer was washed with water and brine, followed by drying with anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-2:1) to afford tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (900 mg).

Aufarbeitung

  1. washthe organic layer was washed with water and brine
  2. dry with materialby drying with anhydrous sodium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-64ad1954f1454d219e50008c89813cd9
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796272B2

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