Réaction #84702

Équation de réaction

ethyl 3-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate

triethylamine

methanesulfonyl chloride

→

title compound

Rendement 97.7%

ethyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)cyclohexanecarboxylate

Rendement 97.7%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   LavageThe solution was washed with water (100 mL×3) and brine
2. 2
   Séchagedried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Mode opératoire

To a solution of Racemate-ethyl 3-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate (12.0 g, 42 mmol) and triethylamine (12.7 g, 126 mmol) in dichloromethane (150 mL) was added methanesulfonyl chloride (9.5 g, 84 mmol) dropwise at 0° C., and the mixture was stirred at 0° C. for 3 hours. The solution was washed with water (100 mL×3) and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound (15 g, crude) as a yellow oil. MS (ES+) C15H27NO7S requires: 365, found: 266 [M+H−100]+.

Source