Water → 2-(Benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propyl methanesulfonate

Participants

Reaction Steps

To a solution of benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-hydroxypropan-2-ylcarbamate (668 mg, 2.1 mmol, 1 eq.), TEA (638 mg, 6.3 mmol, 3 eq.) in CH2Cl2 (100 mL) was added dropwise MsCl (289 mg, 2.52 mmol, 1.2 eq.) at 0-5° C. The resulting mixture was stirred for 2 hrs. Then the mixture was poured into water (20 mL) and extracted with CH2Cl2 (20 mL×4). The organic phase was combined and evaporated to give 2-(benzyloxycarbonylamino)-3-(bicyclo[2.2.2]octan-1-yl)propyl methanesulfonate (1.1 g, crude) as oil, which was used in the next step without further purification.

Provenance & Evidence