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

HRID 264453Notes

Reaction equation

HRID 264453 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][C@@H: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.CN(C)C=O.O>[N:30]([C@H: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

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 10681969(S)-1-(7-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

Product 1

HCID 53984154(R)-1-(2-azido-propyl)-7-chloro-1,4-dihydro-indeno[1,2-b]pyrroleYield 49%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.97 ml of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 1.55 g of (S)-1-(7-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 3.5 ml of triethyl-amine in 40 ml of diohloromethane and the mixture was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 200 ml of dichloromethane, washed twice with 70 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 70 ml of dichloromethane. The combined organic phases were washed to 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 815 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 ethyl acetate 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). 833 mg (49%) of (R)-1-(2-azido-propyl)-7-chloro-1,4-dihydro-indeno[1,2-b]pyrrole were 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. extractionthe combined aqueous phases were extracted once with 70 ml of dichloromethane
  4. washThe combined organic phases were washed to 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
  11. extractionextracted twice with 140 ml of ethyl acetate 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-7c31f9648b3f4964b72f43b5746ca41f
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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