Hydrochloric Acid → 1-Tert-butyl 3-methyl 4-hydroxypiperidine-1,3-dicarboxylate

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Reaction Steps

In a flask, methanol (1.425 mL) and triethylamine (0.0277 g, 0.274 mmol) was added to 1-tert-butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (0.0587 g, 0.228 mmol). The reaction was allowed to stir at room temperature for 15 minutes. Sodium borohydride (0.0285 g, 0.753 mmol) was added to the flask one portion. The reaction was allowed to stir at room temperature for an additional hour. Using 1N hydrochloric acid, the reaction was neutralized to pH 7 and then concentrated under vacuo. Water (2 mL) was used to dissolve the residue. The mixture was extracted using dichloromethane (3×2 mL). The extracts were combined, washed with saturated sodium bicarbonate, dried using sodium sulfate, and concentrated under vacuo. The crude product was progressed to the next step without further purification.

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