Triethylamine → (RS)-1-(2-azido-propyl)-5-methoxy-1,4-dihydro-indeno[1,2-b]-pyrrole

HRID 264570Notes

Reaction equation

HRID 264570 reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:9]=1[CH2:10][C:11]1[CH:15]=[CH:14][N:13]([CH2:16][CH:17](O)[CH3:18])[C:12]=12.C(N(CC)CC)C.[N-:31]=[N+:32]=[N-:33].[Na+]>ClCCl.C(OCC)C.CN(C)C=O.O>[N:31]([CH:17]([CH3:18])[CH2:16][N:13]1[CH:14]=[CH:15][C:11]2[CH2:10][C:9]3[C:20]([C:12]1=2)=[CH:21][CH:22]=[CH:23][C:8]=3[O:7][CH3:6])=[N+:32]=[N-:33]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 10562194(RS)-1-(5-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

Product 1

HCID 10683333(RS)-1-(2-azido-propyl)-5-methoxy-1,4-dihydro-indeno[1,2-b]-pyrroleYield 73%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.45 ml of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 0.7 g of (RS)-1-(5-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 1.6 ml of triethylamine in 20 ml of dichloromethane and the mixture was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 200 ml of diethyl ether, washed twice with 70 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 140 ml of diethyl ether. The combined organic phases were washed with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 20 ml of anhydrous dimethylformamide, treated with 366 mg of sodium azide and the reaction mixture was heated to 60° while stirring for 18 hours. After cooling, the solution was poured into 140 ml of water and extracted twice with 140 ml of diethyl ether each time. The combined organic phases were washed once with 140 ml of water and once with 140 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (toluene). 0.55 g (73%) of (RS)-1-(2-azido-propyl)-5-methoxy-1,4-dihydro-indeno[1,2-b]-pyrrole was obtained as a colorless oil.

Workup

  1. stirringthe mixture was stirred at this temperature for an additional 1.5 hours
  2. washwashed twice with 70 ml of saturated sodium hydrogen carbonate solution each time
  3. extractionthe combined aqueous phases were extracted once with 140 ml of diethyl ether
  4. washThe combined organic phases were washed with 70 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in a vacuum
  7. customThe brown oil obtained
  8. temperaturethe reaction mixture was heated to 60°
  9. stirringwhile stirring for 18 hours
  10. temperatureAfter cooling
  11. extractionextracted twice with 140 ml of diethyl ether each time
  12. washThe combined organic phases were washed once with 140 ml of water and once with 140 ml of saturated sodium chloride solution
  13. dry with materialdried over magnesium sulfate
  14. concentrationthe solution was concentrated in a vacuum
  15. customThe brown oil obtained
  16. customwas purified by column chromatography on silica gel (toluene)

Sources & evidence

ORD record
ord-e4efa3e0dd1d44ffbd3afd0a3d223c80
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

Loading…