Methanol → rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid

Participants

Reaction Steps

276 mg of rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid tert.-butyl ester were dissolved in EtOH (1.7 mL) and treated with LiOH.H2O (181 mg), H2O (0.55 mL) and MeOH (1.65 mL). The reaction mixture was stirred at rt for 4 days and concentrated in vacuo. The resulting aq. residue was partitioned between water and Et2O. The aq. layer was separated, acidified with 25%-HCl, and extracted with DCM. The organic phase was dried over anh. Na2SO4 and concentrated to give 205 mg of rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid as a white solid.

Provenance & Evidence