(Diethylamino)sulfur trifluoride → Tert-butyl (2-fluoro-2-methylpropyl)carbamate

HRID 598045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598045
O[C:2]([CH3:13])([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(S(F)(F)[F:20])CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[F:20][C:2]([CH3:13])([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Komponenten

5

Edukt 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 11106129tert-Butyl 2-hydroxy-2-methylpropylcarbamate

Produkt 1

HCID 72698934Tert-butyl (2-fluoro-2-methylpropyl)carbamateAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 2-hydroxy-2-methylpropylcarbamate (19.2 g, 101 mmol) in dichloromethane (500 mL) was stirred at −78° C. under a nitrogen atmosphere, and (diethylamino)sulfur trifluoride (DAST)(18.0 g, 112 mmol) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight. Saturated aqueous sodium bicarbonate (150 mL) was added. The organic layer was then separated and washed sequentially with saturated aqueous sodium bicarbonate (150 mL), water (150 mL), and brine (150 mL); dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The resulting oil was purified by automated flash chromatography (FLASH 65I cartridge, eluting with 10% ethyl acetate in hexane) to provide 13.7 g of tert-butyl 2-fluoro-2-methylpropylcarbamate as a light yellow oil that crystallized overnight.

Aufarbeitung

  1. customThe organic layer was then separated
  2. washwashed sequentially with saturated aqueous sodium bicarbonate (150 mL), water (150 mL), and brine (150 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationand concentrated under reduced pressure
  6. customThe resulting oil was purified by automated flash chromatography (FLASH 65I cartridge, eluting with 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7e5ba8712eef419ab41071692cf4dab3
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897609B2

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