Pyridine → 1-Methoxycarbonyloxy-3-adamantanol

HRID 1296378Notes

Reaction equation

HRID 1296378 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 was 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-902c2da042cf425598299ecf66405fd8
Source dataset
uspto-grants-2007_07
Patent number
USRE039744E1

Reaction notes

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