Reacción #159303

Ecuación de reacción

5-hydroxy-2-adamantanone

NaBH4

→

1,4-dihydroxyadamantane

Disolventes

MeOH

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated to dryness
2. 2
   Lavadowashed with water (25 mL) and brine (25 mL)
3. 3
   Secadodried over Na2SO4
4. 4
   workup.WAITleft the title compound as a white solid (4.88 g, 94%)
5. 5
   workup.ADDITIONas a 1:1 mixture of cis and trans isomers

Procedimiento

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.

Fuente