Water → (2R,4R)-tert-butyl 4-(benzyloxymethoxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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Reaction Steps

To a mixture of (2R,4R)-1-tert-butyl 2-methyl 4-(benzyloxymethoxy)pyrrolidine-1,2-dicarboxylate (2.29 g, 6.27 mmol, EXAMPLE 79 Step 1) and lithium chloride (586 mg, 13.8 mmol) in ethanol (25 mL) was added sodium borohydride (522 mg, 13.8 mmol) at 0° C., and the mixture was stirred at room temperature for 24 h. Then, the mixture was poured into water, and the aqueous layer was extracted with ethyl acetate three times. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 1:2 to 2:3) to give 1.72 g (81%) of the title compound as a colorless oil.

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