Triethylamine → (RS)-1-(2-azido-propyl)-7-chloro-1,4-dihydro-indeno[1,2-b]-pyrrole

HRID 264432Notes

Reaction equation

HRID 264432 reaction equation
CS(Cl)(=O)=O.[Cl:6][C:7]1[CH:22]=[C:21]2[C:10]([CH2:11][C:12]3[CH:16]=[CH:15][N:14]([CH2:17][CH:18](O)[CH3:19])[C:13]=32)=[CH:9][CH:8]=1.C(N(CC)CC)C.[N-:30]=[N+:31]=[N-:32].[Na+]>ClCCl.C(OCC)C.CN(C)C=O.O>[N:30]([CH:18]([CH3:19])[CH2:17][N:14]1[CH:15]=[CH:16][C:12]2[CH2:11][C:10]3[C:21]([C:13]1=2)=[CH:22][C:7]([Cl:6])=[CH:8][CH:9]=3)=[N+:31]=[N-:32]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 19036406(RS)-1-(7-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

Product 1

HCID 19036487(RS)-1-(2-azido-propyl)-7-chloro-1,4-dihydro-indeno[1,2-b]-pyrroleYield 60%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.95 ml of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0° C., of 1.52 g of (RS)-1-(7-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 3.4 ml of triethylamine in 40 ml of dichoromethane and the mixture was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 280 ml of diethyl ether, washed twice with 70 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were washed once with 70 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 30 ml of anhydrous dimethylformamide, treated with 718 mg of sodium azide and the reaction mixture was heated to 60° for 17 hours while stirring. After cooling the solution was poured into 140 ml of water and extracted twice with 140 ml of diethyl ether each time and once with 140 ml of ethyl acetate. 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). 1.0 g (60%) of (RS)-1-(2-azido-propyl)-7-chloro-1,4-dihydro-indeno[1,2-b]-pyrrole was obtained as an 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. washthe combined aqueous phases were washed once with 70 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° for 17 hours
  9. stirringwhile stirring
  10. temperatureAfter cooling the solution
  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-9d9f8de65f33447cb22c0208b579b5ab
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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