3-Hydroxyadamantane-1-carboxylic acid → 3-(Hydroxymethyl)adamantan-1-ol

HRID 1937250Notes

Reaction equation

HRID 1937250 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][C:12]([OH:20])([CH2:13]3)[CH2:11]1)[CH2:17]2)(O)=[O:8]>O1CCCC1>[OH:8][CH2:7][C:10]12[CH2:17][CH:16]3[CH2:15][CH:14]([CH2:13][C:12]([OH:20])([CH2:18]3)[CH2:11]1)[CH2:19]2

Participants

4

Reactant 2

HCID 27365183-Hydroxyadamantane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 120704753-(Hydroxymethyl)adamantan-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, 15 mmole of lithium aluminium hydride was suspended into 15 mL of tetrahydrofurane (THF). To the resultant mixture was slowly added 10 mmole of 1-carboxy-3-adamantanol obtained by the method of Example 2 while keeping the temperature of the mixture at 10° C. or below by using an ice bath. After warming the mixture to room temperature, the mixture was refluxed for 16 hours. As a result, 1-hydroxymethyl-3-adamantanol (yield 95%) was obtained. The conversion of 1-carboxy-3-adamantanol was 99%.

Workup

  1. customobtained by the method of Example 2
  2. customat 10° C. or below
  3. temperaturethe mixture was refluxed for 16 hours

Sources & evidence

ORD record
ord-46b5800ad96a4c39b8bd0ffe1de985e7
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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