Methanol → HCID 15782683, compound

HRID 992159

Reaction equation

HRID 992159 reaction equation
[C:1](Cl)(=O)C.C(N(CC)CC)C.CO.[C:14]([C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][C:19]([N+:27]([O-:29])=[O:28])([CH2:20]3)[CH2:18]1)[CH2:24]2)([OH:16])=[O:15]>CN(C=O)C>[CH3:1][O:15][C:14]([C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][C:19]([N+:27]([O-:29])=[O:28])([CH2:20]3)[CH2:18]1)[CH2:24]2)=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 392393-Nitrotricyclo(3.3.1.13,7)decane-1-carboxylic acid

Product 1

HCID 15782683HCID 15782683, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of nitrogen, 10 mmole of 1-carboxy-3-nitroadamantane obtained by the method of Example 42 was dissolved in 10ml of DMF. To the mixture, 15 mmole of acetyl chloride was added dropwise over 30 minutes. The mixture was heated to begin to reflux around the conclusion of the addition. After refluxing for 2 hours, the mixture was cooled, 20 mmole of triethylamine was added, and then 11 mmole of methanol was added dropwise over 30 minutes while retaining the temperature of the mixture at 10° C. or less followed by stirring for more 2 hours. As a result, the conversion of 1-carboxy-3-nitroadamantane was 99%, and 1-methoxycarbonyl-3-nitroadamantane (yield 95%) was formed.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux around the conclusion of the addition
  3. temperatureAfter refluxing for 2 hours
  4. temperaturethe mixture was cooled
  5. customat 10° C. or less

Sources & evidence

ORD record
ord-2797b2fbc30c4e2f9176f399c466e35e
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Linked notes

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