Chloride → Methyl 3-hydroxyadamantane-1-carboxylate

HRID 1937249Notes

Reaction equation

HRID 1937249 reaction equation
[Cl-].[CH2:2](N(CC)CC)C.CO.[C:11]([C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][C:16]([OH:24])([CH2:17]3)[CH2:15]1)[CH2:21]2)([OH:13])=[O:12]>CN(C=O)C>[CH3:2][O:12][C:11]([C:14]12[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][C:16]([OH:24])([CH2:22]3)[CH2:15]1)[CH2:23]2)=[O:13]

Participants

6

Reactant 4

HCID 312ChlorideHCID 887MethanolHCID 8471TriethylamineHCID 27365183-Hydroxyadamantane-1-carboxylic acid

Product 1

HCID 144304Methyl 3-hydroxyadamantane-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of nitrogen, 10 mmole of 1-carboxy-3-adamantanol obtained by the method of Example 2 was dissolved in 10 ml of DMF. To the mixture, 15 mmole of tionyl chloride was added dropwise over 30 minutes while heating the mixture to the reflux temperature so as to begin to reflux at about the time the addition is finished. After refluxing for 2 hours, the mixture was cooled. To the mixture, 20 mmole of triethylamine was added and 11 mmole of methanol was added dropwise over 30 minutes while keeping the temperature of the solution at 10° C. or below, and the mixture was stirred for another 2 hours. As a result, the conversion of 1-carboxy-3-adamantanol was 99%, and 1-methoxycarbonyl-3-adamantanol (yield 95%) was formed.

Workup

  1. temperaturewhile heating the mixture to the reflux temperature so as
  2. temperatureto reflux at about the time
  3. additionthe addition
  4. temperatureAfter refluxing for 2 hours
  5. temperaturethe mixture was cooled
  6. customat 10° C. or below

Sources & evidence

ORD record
ord-82193f55631443e19326582a4be65fde
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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