Sodium Hydroxide → 3-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester

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Reaction Steps

To a mixture of azetidine-1,3-dicarboxylic acid monobenzyl ester (6.4 g) in THF (200 mL) was added BH3.THF (6 eq, 163 mL, 1M solution) dropwise via an addition funnel at −40 C under an N2 atmosphere. The solution was warmed to RT and stirred overnight. To the reaction, 5N NaOH (50 mL) was added and then concentrated under vacuum. The resulting aqueous solution was extracted with Et2O (3×100 mL). The organic layer was dried over Na2SO4 and evaporated to give the title compound which was used without further purification.

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