Sodium Hydroxide → Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate

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Reaction Steps

After dissolving dimethyl 1,3-adamantanedicarboxylate (1.00 g, 3.96 mmol) in tetrahydrofuran (5 mL), diisobutylaluminum hydride (0.95 M; 5.0 mL, 4.75 mmol) was added dropwise while cooling on ice, and then the mixture was further stirred for 3 hours while cooling on ice. After the reaction, water (0.2 mL) and then aqueous 15% NaOH (0.2 mL) were added dropwise at room temperature, and the mixture was stirred for 30 minutes. Next, water (0.6 mL) and anhydrous magnesium sulfate were added and stirred therewith, and the insoluble portion was filtered out. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to chromatography (50 g Merck Art. 9385, hexane:ethyl acetate=3:2) to obtain the title compound as a colorless oil (0.1648 g, 0.735 mmole) (19% yield).

Provenance & Evidence