Reaction #69129

Reaction equation

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

Triethylamine

methanesulfonylchloride

→

compound

Yield 93.0%

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

Yield 93.0%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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