4-Oxoadamantane-1-carboxylic acid → 4-hydroxyadamantane-1-carboxylic Acid

HRID 1424566Notes

Reaction equation

HRID 1424566 reaction equation
[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3([C:12]([OH:14])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([OH:14])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2

Participants

4

Reactant 2

HCID 28425154-Oxoadamantane-1-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 45525374-hydroxyadamantane-1-carboxylic AcidYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 4-oxoadamantane-1-carboxylic acid (4.42 g, 22.8 mmol) in MeOH (100 mL) was cooled in an ice bath and NaBH4 tablets (4×1 g, 106 mmol) were added at 15 min intervals. The ice bath was allowed to melt and the mixture was stirred overnight at rt and concentrated under reduced pressure. The residue was diluted with 5% aq HCl (100 mL) and extracted with ether (2×125 mL). The combined ether extracts were dried over MgSO4 and concentrated to give 4-hydroxyadamantane-1-carboxylic acid (4.47 g, quant) as an off-white solid which was used directly.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with 5% aq HCl (100 mL)
  3. extractionextracted with ether (2×125 mL)
  4. dry with materialThe combined ether extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-880206f3c6bd4f38833f06fba606d756
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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