Reaktion #597941

Reaktionsgleichung

4-(4-chlorophenyl)cyclohexanecarboxylic acid

triethylamine

diphenyl phosphorazidate

tert-butanol

→

title compound

Ausbeute 57.0%

tert-butyl 4-(4-chlorophenyl)cyclohexylcarbamate

Ausbeute 57.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was heated
2. 2
   Temperaturto reflux for 16 hours
3. 3
   Waschenwashed with 1M hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride
4. 4
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Wascheneluting with a linear gradient of 5-50% EtOAc in hexanes

Vorschrift

To a solution of 4-(4-chlorophenyl)cyclohexanecarboxylic acid (1.01 g, 4.231 mmol) and triethylamine (0.5897 ml, 4.231 mmol) in tert-butanol (22 ml) was added diphenyl phosphorazidate (0.9147 ml, 4.231 mmol), and the reaction was heated to reflux for 16 hours. The reaction was diluted with EtOAc and washed with 1M hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was on a Biotage SP1 system eluting with a linear gradient of 5-50% EtOAc in hexanes to yield 760 mg of the title compound (57% yield).

Quelle