Tetrahydrofuran → 4-oxoadamantane-1-carboxamide

HRID 589651Notes

Reaction equation

HRID 589651 reaction equation
[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3([C:12]([OH:14])=O)[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C(Cl)(=O)C(Cl)=O.O.[NH3:22].C1COCC1>CN(C=O)C.O>[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3([C:12]([NH2:22])=[O:14])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 28425154-Oxoadamantane-1-carboxylic acidHCID 12896473Azane;hydrate

Product 1

HCID 28434324-oxoadamantane-1-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent

Procedure

50 g of 4-oxoadamantane-1-carboxylic acid (1) was dissolved in 300 mL of MC and to the resulting solution was slowly added dropwise 30 mL of oxalic chloride. Then, five drops of DMF were added and the resulting mixture was stirred at room temperature for two hours, distilled under a reduced pressure, and then vacuum-dried. The compound as vacuum-dried was dissolved in 150 mL of anhydrous THF and the resulting solution was added dropwise to a solution prepared by mixing 60 mL of ammonia water and 150 mL of THF. This reaction was extremely exothermic and thus the reactor cooled with iced water. After being stirred for 30 minutes, solids in the reaction product were filtered off by using MC, and the organic solution being collected was dried over MgSO4 and then filtered and dried under a reduced pressure. The resulting product was recrystallized with a solution of MeOH and ether to provide 43 g of 4-oxoadamantane-1-carboxamide (2).

Workup

  1. distillationdistilled under a reduced pressure
  2. customvacuum-dried
  3. customThe compound as vacuum-dried
  4. dissolutionwas dissolved in 150 mL of anhydrous THF
  5. additionthe resulting solution was added dropwise to a solution
  6. customprepared
  7. stirringAfter being stirred for 30 minutes
  8. filtrationsolids in the reaction product were filtered off
  9. customthe organic solution being collected
  10. dry with materialwas dried over MgSO4
  11. filtrationfiltered
  12. customdried under a reduced pressure
  13. customThe resulting product was recrystallized with a solution of MeOH and ether

Sources & evidence

ORD record
ord-9dbb3ee201cf4640a295ef64333ef074
Source dataset
uspto-grants-2016_01
Patent number
US09233957B2

Reaction notes

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