3-Oxabicyclo(3.1.0)hexane-2,4-dione → (1R,5S)-3-(2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-3-aza-bicyclo[3.1.0]-hexane-2,4-dione

HRID 1093998Notes

Reaction equation

HRID 1093998 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[CH:13]12[CH2:18][CH:17]1[C:16](=[O:19])[O:15][C:14]2=O>C(O)(=O)C>[O:12]=[C:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][N:1]3[C:14](=[O:15])[C@@H:13]4[C@@H:17]([CH2:18]4)[C:16]3=[O:19])[CH:4]=2)[NH:8]1

Participants

4

Reactant 2

HCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 179825555-(Aminomethyl)indolin-2-one

Product 1

HCID 66636255(1R,5S)-3-(2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-3-aza-bicyclo[3.1.0]-hexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the compound obtained in Step C (15 mmoles) and 3-oxa-bicyclo[3.1.0]-hexane-2,4-dione (22.5 mmoles) in acetic acid (60 ml) is heated at reflux for 48 hours. The mixture is brought to ambient temperature and the solid formed is filtered off to yield the title product, which is used directly in the next reaction.

Workup

  1. temperatureat reflux for 48 hours
  2. customis brought to ambient temperature
  3. customthe solid formed
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-496e977a69bf4de9909cb4a7cb1901ae
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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