N-(4-hydroxy-1-adamantyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 1-acetamido-4-oxoadamantane (420 mg, 2.0 mmol) in MeOH (20 mL) was cooled in an ice bath and an NaBH4 caplet (1.0 g, 26 mmol) was added. The mixture was stirred over the weekend at rt and evaporated to dryness. The residue was taken up in EtOAc (90 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over MgSO4. Removal of the solvent left 1-acetamido-4-hydroxyadamantane (170 mg, 40%). evaporated to dryness washed with 5% aq HCl (20 mL) dried over MgSO4 Removal of the solvent left 1-acetamido-4-hydroxyadamantane (170 mg, 40%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 1-acetamido-4-oxoadamantane (420 mg, 2.0 mmol) in MeOH (20 mL) was cooled in an ice bath and an NaBH4 caplet (1.0 g, 26 mmol) was added. The mixture was stirred over the weekend at rt and evaporated to dryness. The residue was taken up in EtOAc (90 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over MgSO4. Removal of the solvent left 1-acetamido-4-hydroxyadamantane (170 mg, 40%). evaporated to dryness washed with 5% aq HCl (20 mL) dried over MgSO4 Removal of the solvent left 1-acetamido-4-hydroxyadamantane (170 mg, 40%)