5-Bromoindole → Phenylmethyl (2R)-2-((5-bromo-1H-indol-3-yl)carbonyl)-1-pyrrolidinecarboxylate

HRID 1441069노트

반응식

HRID 1441069 반응식
C([Mg]Br)C.[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[CH2:15]([O:22][C:23]([N:25]1[CH2:32][CH2:31][CH2:30][C@@H:26]1[C:27](O)=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>C(OCC)C>[CH2:15]([O:22][C:23]([N:25]1[CH2:32][CH2:31][CH2:30][C@@H:26]1[C:27]([C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([Br:5])[CH:7]=2)[NH:11][CH:10]=1)=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 249055-BromoindoleHCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylateHCID 516892Sodium BicarbonateHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 11224090Phenylmethyl (2R)-2-((5-bromo-1H-indol-3-yl)carbonyl)-1-pyrrolidinecarboxylate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매4회

실험 절차

In a separate flask a solution of ethylmagnesium bromide (1.4 ml of a 3M solution in diethyl ether) was added dropwise over 5 minutes to a stirred solution of 5-bromoindole (0.75 g) in dry diethyl ether (18 ml). The mixture was stirred at room temperature for 10 minutes, heated under reflux for 2 hours, then cooled to -30° C. A solution of the above acid chloride of N-benzyloxycarbonyI-D-proline in dry diethyl ether (4 ml) was then added dropwise with stirring and stirring was continued for a further 1 hour. Diethyl ether (12.5 ml) and saturated aqueous sodium bicarbonate (6.5 ml) were added and the reaction was allowed to warm to room temperature. Stirring was continued for a further 10 minutes and the mixture was filtered. The solid was washed with ethyl acetate and the combined filtrate and washings were washed with water then brine and dried (MgSO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with ethyl acetate gave, after combination and evaporation of the appropriate fractions, the title compound as a foam, (0.82 g). Found: C,58.85; H,4.51; N,6.38; C21H19BrN2O3 requires: C,59.02; H,4.48; N,6.56%.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled to -30° C
  4. stirringwith stirring
  5. stirringstirring
  6. waitwas continued for a further 1 hour
  7. temperatureto warm to room temperature
  8. stirringStirring
  9. waitwas continued for a further 10 minutes
  10. filtrationthe mixture was filtered
  11. washThe solid was washed with ethyl acetate
  12. washthe combined filtrate and washings were washed with water
  13. dry with materialbrine and dried (MgSO4)
  14. customEvaporation of the solvent
  15. customgave an oil which
  16. customwas chromatographed on silica gel
  17. washElution with ethyl acetate
  18. customgave
  19. customafter combination and evaporation of the appropriate fractions

출처 및 근거

ORD 기록
ord-cc91429576714b18a322701681d94c3b
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05502065

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