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

HRID 264395ノート

反応式

HRID 264395 の反応式
CS(Cl)(=O)=O.[CH3:6][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]([CH3:6])=[CH:8][CH:9]=3)=[N+:31]=[N-:32]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 53971660(R)-1-(7-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

生成物 1

HCID 10729494(S)-1-(2-azido-propyl)-7-methyl-1,4-dihydro-indeno[1,2-b]pyrrole収率 50%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

1.8 ml of methanesulfonyl chloride were added dropwise while stirring to a solution, cooled to 0°, of 2.7 g of (R)-1-(7-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 6.7 ml of triethyl-amine in 75 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 dichloromethane, washed twice with 90 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 90 ml of dichloromethane. The combined organic phases were washed with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 70 ml of anhydrous dimethylformamide, treated with 1.55 g of sodium azide and the reaction mixture was heated to 60° for 15 hours while stirring. 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 120 ml of water and once with 120 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). 1.5 g (50%) of (S)-1-(2-azido-propyl)-7-methyl-1,4-dihydro-indeno[1,2-b]pyrrole were obtained as a light yellow oil.

後処理

  1. stirringthe mixture was stirred at this temperature for an additional 1.5 hours
  2. washwashed twice with 90 ml of saturated sodium hydrogen carbonate solution each time
  3. extractionthe combined aqueous phases were extracted once with 90 ml of dichloromethane
  4. washThe combined organic phases were washed with 100 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 15 hours
  9. stirringwhile stirring
  10. temperatureAfter cooling
  11. extractionextracted twice with 150 ml of ethyl acetate each time
  12. washThe combined organic phases were washed once with 120 ml of water and once with 120 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)

出典と根拠

ORDレコード
ord-dc1dcc270c1845bc9d5fddd06866894a
出典データセット
uspto-grants-1997_07
特許番号
US05646173

反応ノート

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