Perchloric Acid → t-butyl octahydro-3-oxo-1H-isoindole-1-carboxylate

HRID 2164223Notes

Reaction equation

HRID 2164223 reaction equation
[O:1]=[C:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH:4]([C:11]([OH:13])=[O:12])[NH:3]1.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[O:1]=[C:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH:4]([C:11]([O:13][C:5]([CH3:10])([CH3:6])[CH3:4])=[O:12])[NH:3]1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 13388635octahydro-3-oxo-1H-isoindole-1-carboxylic acid

Product 1

HCID 13388636t-butyl octahydro-3-oxo-1H-isoindole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent2×

Procedure

The intermediate t-butyl octahydro-3-oxo-1H-isoindole-1-carboxylate is prepared from octahydro-3-oxo-1H-isoindole-carboxylic acid (Example 5) as follows. A mixture of 10 g of this acid and 0.4 ml of 70% perchloric acid in 150 ml of t-butyl acetate is allowed to stand for 2.5 days. An additional 50 ml of t-butyl acetate is added and the reaction is allowed to continue for 15 days. The solution is filtered and poured onto 14 g of 50% sodium hydroxide solution and ice. The product is extracted into ether. Drying and concentration gives a residue which when triturated with hexane gives material, mp 143°-149° C., suitable for further use.

Workup

  1. waitto continue for 15 days
  2. filtrationThe solution is filtered
  3. additionpoured onto 14 g of 50% sodium hydroxide solution and ice
  4. extractionThe product is extracted into ether
  5. customDrying
  6. concentrationconcentration
  7. customgives a residue which when
  8. customtriturated with hexane
  9. customgives material, mp 143°-149° C.

Sources & evidence

ORD record
ord-0b3cca78b1e64b90a433b9bbb884f3f2
Source dataset
uspto-grants-1985_03
Patent number
US04503043

Reaction notes

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