Reaktion #305179

Reaktionsgleichung

[Bis(2-methoxyethyl)amino]sulfur trifluoride

tert-butyl [(4aR,6R,8aS)-8a-(5-bromo-2-fluorophenyl)-6-hydroxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

sodium bicarbonate

→

title compound

tert-butyl [(4aR,6R,8aS)-8a-(5-bromo-2-fluorophenyl)-6-fluoromethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto terminate
2. 2
   Sonstigethe reaction
3. 3
   ExtraktionThe aqueous layer was extracted with ethyl acetate
4. 4
   Trocknenthe organic layer was dried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

[Bis(2-methoxyethyl)amino]sulfur trifluoride (155 μl) was added dropwise to a solution of tert-butyl [(4aR,6R,8aS)-8a-(5-bromo-2-fluorophenyl)-6-hydroxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate (200 mg) in dichloromethane (5.0 ml) at −78° C. The mixture was stirred overnight with gradual heating to room temperature. A sodium bicarbonate solution was added to the reaction mixture to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (145 mg).

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