Réaction #69129

Équation de réaction

Cis-(R)-tert-butyl 1-(4-hydroxycyclohexyl)ethylcarbamate

Triethylamine

methanesulfonylchloride

→

compound

Rendement 93.0%

Cis-(R)-4-(1-(tert-butoxycarbonylamino)ethyl)cyclohexyl methanesulfonate

Rendement 93.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   LavageThe crude mixture was washed with 1M HCl, water
3. 3
   SéchageThe organic extracts were dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

Cis-(R)-tert-butyl 1-(4-hydroxycyclohexyl)ethylcarbamate (575 mg, 2.363 mmol) was dissolved in dichloromethane (10 mL) and cooled to 0° C. under nitrogen. Triethylamine (478.2 mg, 658.7 μL, 4.726 mmol) followed by methanesulfonylchloride (284.2 mg, 192.0 μL, 2.481 mmol) were added dropwise. The reaction mixture was stirred at room temperature for 30 minutes. The crude mixture was washed with 1M HCl, water and a saturated aqueous solution of sodium bicarbonate. The organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to give the compound as a white solid (706 mg, 93% yield).

Source