Water → 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione

HRID 2201669Notes

Reaction equation

HRID 2201669 reaction equation
[CH:1]12[CH2:6][CH:5]1[C:4](=[O:7])[O:3][C:2]2=O.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>C(O)(=O)C>[CH2:9]([N:16]1[C:4](=[O:7])[CH:5]2[CH:1]([CH2:6]2)[C:2]1=[O:3])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dione

Product 1

HCID 27645863-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-oxabicyclo[3.1.0]hexane-2,4-dione (23-1) (20 g, 0.179 mol) was dissolved in acetic acid (100 mL), and benzylamine (28.8 g, 0.269 mol) was added dropwise under cooling in a water bath, after the completion of addition, the temperature was raised to reflux and stirred overnight. The reaction mixture was cooled to room temperature, poured into 1 L of water to precipitate large amount of white solid, filtered, and the filter cake was recrystallized from isopropanol to give Compound 23-2 (27 g).

Workup

  1. temperatureunder cooling in a water bath
  2. additionafter the completion of addition
  3. temperaturethe temperature was raised
  4. temperatureto reflux
  5. customto precipitate large amount of white solid
  6. filtrationfiltered
  7. customthe filter cake was recrystallized from isopropanol

Sources & evidence

ORD record
ord-04d35f800205459689df0c5766682d8a
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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