Triethylamine → (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (275 mg, 1.0 mmol, 1.0 equiv) was dissolved in CH2Cl2 and the mixture was cooled to 0° C. To this solution was added methanesulfonyl chloride (230 mg, 2.0 mmol, 2.0 equiv) and triethylamine (304 mg, 3.0 mmol, 3.0 equiv). The mixture was stirred at 0° C. for 0.5 h. After this time LC/MS showed consumption of the starting material. The mixture was transferred to a separatory funnel and 1.0 M aq HCl added. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The crude (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate was used directly in the next step.

Provenance & Evidence