Sodium borohydride → N-(4-hydroxy-1-adamantyl)acetamide

HRID 1948685

Reaction equation

HRID 1948685 reaction equation
[C:1]([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([C:8]3=[O:15])[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH:8]3[OH:15])[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 5338964N-(4-oxo-1-adamantyl)acetamide

Product 1

HCID 14948121N-(4-hydroxy-1-adamantyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. customevaporated to dryness
  2. washwashed with 5% aq HCl (20 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft 1-acetamido-4-hydroxyadamantane (170 mg, 40%)

Sources & evidence

ORD record
ord-27167e89186c41deb9b3a1d61d6820a6
Source dataset
uspto-grants-2013_03
Patent number
US08399504B2

Linked notes

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