Methanol → Methyl 3-hydroxyadamantane-1-carboxylate

HRID 1978111Notes

Reaction equation

HRID 1978111 reaction equation
[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][C:6]([OH:14])([CH2:7]3)[CH2:5]1)[CH2:11]2)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH2:19](N(CC)CC)C.CO>CN(C=O)C>[CH3:19][O:2][C:1]([C:4]12[CH2:11][CH:10]3[CH2:9][CH:8]([CH2:7][C:6]([OH:14])([CH2:12]3)[CH2:5]1)[CH2:13]2)=[O:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27365183-Hydroxyadamantane-1-carboxylic acid2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 mmol of the 1-carboxy-3-adamantanol produced by the method of Preparation Example 5 under a nitrogen atmosphere was dissolved in 10 ml of DMF, and 15 mmol of thionyl chloride was dropped into the solution for 30 minutes. The temperature was elevated so that the solution starts its reflux at the end of dropping. After two hours of reflux, the reactant mixture was cooled, added 20 mmol of triethylamine, the temperature of the mixture was maintained at 10° C. or below, and 11 mmol of methanol was added dropwise for 30 minutes and stirred for 2 hours. And, at the result, the 1-carboxy-3-adamantanol was converted into a 1-methoxycarbonyl-3-adamantanol (yield: 95%) with a conversion of 99%.

Workup

  1. temperaturereflux at the end
  2. temperatureAfter two hours of reflux
  3. temperaturethe reactant mixture was cooled
  4. temperaturethe temperature of the mixture was maintained at 10° C. or below

Sources & evidence

ORD record
ord-ecb11b79ba67453f854cf6f20bc802b0
Source dataset
uspto-grants-2001_05
Patent number
US06235851B1

Reaction notes

Loading…