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. 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.

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

ORD-Eintrag

ord-332665727a9c47d38002d0e0e7d1de79

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399504B2