Idramantone → Adamantane-1,4-diol

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. Removakl 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.

1. concentrationconcentrated to dryness
2. washwashed with water (25 mL) and brine (25 mL)
3. dry with materialdried over Na2SO4
4. waitleft the title compound as a white solid (4.88 g, 94%)
5. additionas a 1:1 mixture of cis and trans isomers

ORD record

ord-9754412822d547fbb4c6b2f37312bd09

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828985B2