Methanol → (1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol

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Reaction Steps

A mixture of (1RS,4SR,5RS)-4-(4-carbomethoxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (71 mg, 0.24 mM), methanol (3 ml), water (1 ml) and 1 N sodium hydroxide (1 ml) is stirred at room temperature under nitrogen for twenty hours. Most of the methanol is removed in vacuo and the residue is treated with concentrated hydrochloric acid (1 ml) at 0° C. and extracted with ethyl acetate (3×30 ml). The combined organic layers are dried (Na2SO4) and evaporated in vacuo to give a colorless oil. This material is filtered through a silica gel column (3 g) and washed with ether (200 ml). The solvent is removed in vacuo to give (1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (58 mg, 88%) as a colorless oil.

Provenance & Evidence