Reaktion #220314

Reaktionsgleichung

tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]carbamate

Intermediate 7

tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]carbamate

2-amino-1-[1-(trifluoromethyl)cyclopropyl]ethanol

→

title compound

tert-Butyl[(2Z,3R,6S)-6-(2,3-difluorophenyl)-2-({2-hydroxy-2-[1-(trifluoromethyl)cyclopropyl]ethyl}imino)azepan-3-yl]carbamate

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   workup.ADDITIONSaturated aqueous NaHCO3 was added
4. 4
   Extraktionthe mixture was extracted with CH2Cl2 (3×)
5. 5
   TrocknenThe combined organic extracts were dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

Mercury(II) chloride (149 mg, 0.547 mmol) was added to a solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]carbamate (150 mg, 0.421 mmol, described in Intermediate 7), and 2-amino-1-[1-(trifluoromethyl)cyclopropyl]ethanol (569 mg, 3.367 mmol) in ethanol (5 mL) at 60° C. After 10 min, the reaction was allowed to cool to ambient temperature. The mixture was filtered and concentrated under reduced pressure. Saturated aqueous NaHCO3 was added and the mixture was extracted with CH2Cl2 (3×). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=492 (M+1).

Quelle