Octahydroindolizin-7-one → HCID 53944409, compound

HRID 363317Notes

Reaction equation

HRID 363317 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:17]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.[CH2:18]1[CH:26]2[N:21]([CH2:22][CH2:23][C:24](=O)[CH2:25]2)[CH2:20][CH2:19]1>[OH-].[K+].O>[CH2:18]1[CH:26]2[N:21]([CH2:22][CH:23]=[C:24]([C:4]3[CH:5]=[C:6]([CH:17]=[C:2]([OH:1])[CH:3]=3)[CH2:7][N:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:10]=[CH:9]3)[CH2:25]2)[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 11240524Octahydroindolizin-7-oneHCID 53832466HCID 53832466, compound

Product 1

HCID 53944409HCID 53944409, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A mixture of 5-hydroxybenzyl-1H-indole (3.69 g, 16.5 mmol) and 7-octahydroindolizinone (2.98 g, 21.5 mmol) in methanolic potassium hydroxide (10% potassium hydroxide in methanol, 50 ml) was heated to reflux for 3.5 hours. The reaction was diluted with water and the precipitate was collected by filtration. The filter cake was triturated with hot diethyl ether and filtered. The filter cake was recrystallized from methanol and dried to give 1.45 g of tan flakes. (25.8%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3.5 hours
  3. filtrationthe precipitate was collected by filtration
  4. customThe filter cake was triturated with hot diethyl ether
  5. filtrationfiltered
  6. customThe filter cake was recrystallized from methanol
  7. customdried
  8. customto give 1.45 g of tan flakes

Sources & evidence

ORD record
ord-07326b54371d43f5a281be369449f161
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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