Idramantone → Adamantane-1,4-diol

関与物質

反応手順

A stirred solution of 5-hydroxy-2-adamantanone (5.14 g, 30.9 mmol) in MeOH (100 mL) was cooled in an ice bath and three 1-g NaBH4 caplets (3 g, 78 mmol) were added. The mixture was allowed to warm to rt and stirred overnight. The mixture was diluted with 5% aq HCl (20 mL) and concentrated to dryness. The residue was taken up in EtOAc (200 mL), washed with water (25 mL) and brine (25 mL), and dried over Na2SO4. Removal of the solvent left the title compound as a white solid (4.88 g, 94%) as a 1:1 mixture of cis and trans isomers.

情報源と証拠