Water → HCID 19036456, compound

HRID 264500Notes

Reaction equation

HRID 264500 reaction equation
[N:1]([CH:4]([CH3:19])[CH2:5][N:6]1[CH:10]=[CH:9][C:8]2[CH2:11][C:12]3[C:17]([C:7]1=2)=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[N+:2]=[N-:3].[CH:20](Br)([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N:1]([CH:4]([CH3:19])[CH2:5][N:6]1[CH:10]=[CH:9][C:8]2[CH2:11][C:12]3[C:17]([C:7]1=2)=[CH:16][C:15]([O:18][CH:20]([CH3:22])[CH3:21])=[CH:14][CH:13]=3)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 19036449HCID 19036449, compound

Product 1

HCID 19036456HCID 19036456, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.05 g of (RS)-1-(2-azido-propyl)-7-hydroxy-1,4-dihydro-indeno[1,2-b]pyrrole, 0.77 ml of isopropyl bromide and 1.14 g of potassium carbonate in 30 ml of N,N-dimethyl-formamide was heated to 50° for 48 hours. After cooling, the solution was poured into 150 ml of water and extracted twice with 150 ml of ethyl acetate each time. The combined organic phases were washed once with 70 ml of semi-saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The crude product was purified by column chromatography on silica gel (toluene). 0.35 g (28%) of (RS)-1-(2-azido-propyl)-7-iso-propoxy-1,4-dihydro-indeno[1,2-b]pyrrole was obtained as an orange oil which was used directly in the next reaction.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with 150 ml of ethyl acetate each time
  3. washThe combined organic phases were washed once with 70 ml of semi-saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationthe solution was concentrated in a vacuum
  6. customThe crude product was purified by column chromatography on silica gel (toluene)

Sources & evidence

ORD record
ord-b284a49f570e4be39bdd9666f4490f7f
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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