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  (Organic Chemistry)


(RMgX + Ester)


Example 1

MeMgCl (0.567 mL, 1.68 mmol) was added to a stirred suspension of the SM (153 mg, 0.337 mmol) in THF (5 mL) under N2 at 0 C. The reaction mixture was stirred at 0 C for 5 min, then it was warmed to RT and stirred for 2 h. The mixture was quenched with 10% NH4Cl and diluted with EtOAc and 10% MeOH/DCM. The org layer was separated, washed with brine, dried (MgSO4) and concentrated to give 143 mg of a white solid which was triturated with DCM to give 100 mg of material. The material was purified by achiral SFC to provide 74 mg of material. This material was further purified by reverse phase chromatography to provide 28 mg of material which was lyophilized (1:4 ACN/H2O) to provide the product as a white solid. [20 mg, 13%]

[Patent Reference: WO2015144799, page 104, (18.8 MB)]