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

HRID 72114

Reaction equation

HRID 72114 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-b18a689529254733af5ff770d15b2ced
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Linked notes

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