Carbamate → 4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 863537

反応式

HRID 863537 の反応式
C1C=CC=C2C=1C=C1CCCCN12.C(=O)([O-])N.[C:18](Cl)(=O)[C:19](Cl)=[O:20].Cl.[CH3:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH2:35][C:36](=[NH:41])[O:37]C(C)C)=[CH:27]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl.C(OCC)(=O)C>[CH3:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35]2[C:36](=[O:41])[NH:37][C:19](=[O:20])[CH:18]=2)=[CH:27]1

参加物

9

反応物 6

HCID 276CarbamateHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 65578Oxalyl chlorideHCID 108559426,7,8,9-Tetrahydropyrido[1,2-a]indoleHCID 22907276HCID 22907276、化合物

生成物 1

HCID 200846494-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A stirred solution of 770 mg (2.25 mmol) of tert.butyl [1(R or S)-[6,7,8,9-tetrahydropyrido[1,2-a]indol-8(R or S)-yl]-2-methylpropyl]carbamate (diastereomer A) in 30 ml of dichloromethane at 0° C. was treated dropwise with 287 mg (2.4 mmol) of oxalyl chloride. After 5 minutes, the solvent was removed under reduced pressure and the residue was dissolved in 30 ml of dichloromethane and treated with 686 mg (2.57 mmol) of isopropyl 1-methyl-3-indoleacetimidate hydrochloride and 1.02 g (10 mmol) of triethylamine at 0° C. under nitrogen. After warming to room temperature, the solution was stirred for 18 hours, washed with 50 ml of water and dried over magnesium sulfate. The solvent was removed by evaporation and the residue was dissolved in 10 ml of pyridine. The stirred solution was cooled to ice bath temperature and treated dropwise with 664 μl (4.8 mmol) of trifluoroacetic anhydride. After 15 minutes, 50 ml of ethyl acetate was added and the organic phase was washed with water and 2M hydrochloric acid, dried over magnesium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether (1:2) for the elution to give 460 mg of 3-[8(R or S)-[1(R or S)-tert.butoxyformamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione (diastereomer A) as a red solid of melting point 223°-224° C.

後処理

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 30 ml of dichloromethane
  3. washwashed with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. dissolutionthe residue was dissolved in 10 ml of pyridine
  7. temperatureThe stirred solution was cooled to ice bath temperature
  8. waitAfter 15 minutes
  9. washthe organic phase was washed with water and 2M hydrochloric acid
  10. dry with materialdried over magnesium sulfate
  11. customevaporated to dryness
  12. customThe residue was purified by flash chromatography on silica gel
  13. washfor the elution

出典と根拠

ORDレコード
ord-29cd225414aa4b2ab184d8520f4109cc
出典データセット
uspto-grants-1998_02
特許番号
US05721230

関連ノート

読み込み中…