Reaktion #1109899

Reaktionsgleichung

hydrochloric acid

tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate

trimethyl(trifluoromethyl)silane

tetrabutylammonium fluoride

→

title compound

Ausbeute 77.2%

tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(2,2,2-trifluoro-1-hydroxyethyl)-1,4-oxazepane-4-carboxylate

Ausbeute 77.2%

Lösungsmittel

water

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture was further stirred for 3 hr
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe extract was washed with distilled water and brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Vorschrift

To a solution (2.6 mL) of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate (100 mg) in THF were added a solution (1.0 M, 0.534 mL) of trimethyl(trifluoromethyl)silane (190 mg) and tetrabutylammonium fluoride in THF under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1 M hydrochloric acid (0.5 ml), and the mixture was further stirred for 3 hr. Distilled water was added, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (91.7 mg).

Quelle