Methyl iodide → (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethyl-cyclopentanecarboxylic acid ethyl ester

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To a solution of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester (Example 68/69 step 4, epimeric mixture, 509 mg) in iodomethane (24 g) was added silver oxide (3.9 g) in several portions over 8 days. After 12 days at room temperature, the reaction mixture was concentrated in vacuo, diluted with dichloromethane, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/EtOAc (1:0 to 9:1 v/v) as eluant to afford the title compound (228 mg, 43%) as light yellow oil. MS (EI): 317.1 (M+H)+.

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