tert-butyl N-[(1R)-3-hydroxy-1-phenylpropyl]carbamate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (R)-tert-Butyl 3-hydroxy-1-phenylpropylcarbamate (Intermediate 60, 258 mg, 1.03 mmol) was dissolved in THF under nitrogen at 0° C. NaH was added and the reaction mixture was stirred at 0° C. for 10 min. MeI was added and the reaction mixture was stirred at room temperature for 30 min. then quenched with sat. aq. Na2SO4 and extracted with Et2O. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified via column chromatography using a biotage SP1 25+M column with a gradient 50% EtOAc in heptane calculated from TLC. Product fractions were combined and concentrated to give the title compound as a white solid (78 mg, 29%). LCMS=[M+H]=266 the reaction mixture was stirred at room temperature for 30 min. then quenched with sat. aq. Na2SO4 extracted with Et2O The organic layer was dried over MgSO4 filtered concentrated in vacuo The crude material was purified via column chromatography concentrated