反应详情

A stirred solution of 2-(trimethylsilyl)ethyl (S)-2-(3-benzoylcyclohexanecarboxamido)-3-cyclohexylpropylmethylcarbamate (111 mg, 0.21 mmol) in dry THF (2 mL) was cooled to −70° C. and methoxybutylmagnesium chloride in THF (0.5 mL of 2 M, 1.0 mmol) was added dropwise over 2 min. The cooling bath was allowed to expire and the mixture was stirred as it warmed to rt. After 2 h, the mixture was poured into sat'd aqueous NaHCO3 (20 mL) and sat'd aqueous NH4Cl (20 mL) was added. The mixture was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4 and evaporated under reduced pressure to leave crude 2-(trimethylsilyl)ethyl (S)-2-(3-(1-hydroxy-5-methoxy-1-phenylpentyl)cyclohexanecarboxamido)-3-cyclohexylpropyl-methylcarbamate as an oil (124 mg, 95%). MS ESI +ve m/z 617 (M+1).

1. additionwas added
2. extractionThe mixture was extracted with EtOAc (2×50 mL)
3. washThe combined organic extracts were washed with brine (15 mL)
4. dry with materialdried over Na2SO4
5. customevaporated under reduced pressure