Perchloric Acid → Ethyl 3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

HRID 974921Notes

Reaction equation

HRID 974921 reaction equation
O1CCCCC1[N:7]1[O:14][CH2:13][CH:12]2[CH:8]1[CH2:9][N:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11]2.Cl(O)(=O)(=O)=O.C[O-].[Na+]>C(O)C>[CH:8]12[CH2:9][N:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH:12]1[CH2:13][O:14][NH:7]2

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 10942334Sodium MethoxideHCID 15070014Ethyl 2-(tetrahydropyran-2-yl)-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

Product 1

HCID 15070015Ethyl 3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15 g (55.5 mmol) of ethyl 2-(tetrahydropyran-2-yl)-3-oxa-2,7-diazabicyclo[3.3.0]octane-7-carboxylate are heated under reflux with 8.25 g (56 mmol) of 70% strength perchloric acid in 100 ml of ethanol for 30 minutes. 10.5 g (58 mmol) of 30 strength sodium methylate solution are added, the mixture is concentrated, the residue is taken up in water and the solution is saturated with K2CO3 and extracted with CHCl3. The extract is dried over K2CO3 and concentrated and the residue is distilled.

Workup

  1. concentrationthe mixture is concentrated
  2. extractionextracted with CHCl3
  3. dry with materialThe extract is dried over K2CO3
  4. concentrationconcentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-8732cee5b9634c788d58b04b09f37483
Source dataset
uspto-grants-1997_03
Patent number
US05607942

Reaction notes

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