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 44278Notes

Reaction equation

HRID 44278 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-82bbcddba0ae4cb4bd9c50f2aa200ad6
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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