Ethyl Acetate → tert-Butyl 3-oxocyclobutylcarbamate

HRID 577739Notes

Reaction equation

HRID 577739 reaction equation
C=[C:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1.[O:14]=[O+][O-].CCOC(C)=O>C(Cl)Cl.CO>[O:14]=[C:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24823OzoneHCID 28875369tert-butyl N-(3-methylidenecyclobutyl)carbamate

Product 1

HCID 23374584tert-Butyl 3-oxocyclobutylcarbamateYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3-methylidenecyclobutyl)carbamate (165 g, 0.91 mol) in CH2Cl2 (1000 mL) and MeOH (1000 mL) was bubbled O3 at −78° C. until the solution turned blue. TLC (petroleum ether:EtOAc=10:1) showed that the starting material was consumed completely. Nitrogen gas was then bubbled through the reaction to remove excess O3, and then the mixture was quenched with Me2S (200 mL) and stirred for an hour. The solution was concentrated to give a residue, which was washed with sat. NaHCO3 and water to yield the title compound (118 g, 70% yield) as a white solid.

Workup

  1. customwas consumed completely
  2. customNitrogen gas was then bubbled through the reaction
  3. customto remove excess O3
  4. customthe mixture was quenched with Me2S (200 mL)
  5. concentrationThe solution was concentrated
  6. customto give a residue, which
  7. washwas washed with sat. NaHCO3 and water

Sources & evidence

ORD record
ord-dd693068411d44fca9be2f3d09937fc3
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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