Pyridine → 1-Methoxycarbonyloxy-3-adamantanol

HRID 1937252Notes

Reaction equation

HRID 1937252 reaction equation
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2.N1C=CC=CC=1.[CH3:19][O:20][C:21](Cl)=[O:22]>CN(C=O)C>[CH3:19][O:20][C:21]([O:12][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 5738291,3-Adamantanediol2×

Product 1

HCID 224635541-Methoxycarbonyloxy-3-adamantanolYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3-adamantanediol and 12 mmole of pyridine were dissolved in 10 mL of DMF. To the mixture, 11 mmole of methoxycarbonyl chloride was added dropwise with stirring at room temperature. Cooling of the resultant mixture with ice was started at about the time exothermic reaction began. When the exothermic reaction is completed, the mixture was heated to 60° C. and then stirred for one hour. As a result, the conversion of 1,3-adamantanediol was 99% and 1-methoxycarbonyloxy-3-adamantanol (yield 85%) was formed.

Workup

  1. customwas started at about the time exothermic reaction
  2. customWhen the exothermic reaction
  3. temperaturethe mixture was heated to 60° C.
  4. stirringstirred for one hour

Sources & evidence

ORD record
ord-add65b2bb09344348849b4e2c76f557d
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

Loading…