5-Bromo-1-(triisopropylsilyl)-1H-indole → 3-[hydroxy-(1-triisopropylsilanyl-1H-indol-5-yl)-methyl]-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester

HRID 1895005

반응식

HRID 1895005 반응식
C([Li])(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:11]=[CH:10]2.[CH3:26][O:27][C:28]([N:30]1[CH2:34][CH2:33][C:32]([CH:41]=[O:42])([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31]1)=[O:29]>C1COCC1>[CH3:26][O:27][C:28]([N:30]1[CH2:34][CH2:33][C:32]([CH:41]([OH:42])[C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([Si:16]([CH:20]([CH3:21])[CH3:22])([CH:23]([CH3:25])[CH3:24])[CH:17]([CH3:19])[CH3:18])[CH:11]=[CH:10]3)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31]1)=[O:29]

참가 물질

5

반응물 3

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indoleHCID 580172733-Formyl-3-phenyl-pyrrolidine-1-carboxylic acid methyl esterHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 580172393-[hydroxy-(1-triisopropylsilanyl-1H-indol-5-yl)-methyl]-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

tert-Butyllithium (1.7 M in pentane, 8.9 mL, 15.10 mmol) was added at −78° C., under nitrogen atmosphere to a solution of 5-bromo-1-triisopropylsilanyl-1H-indole (2.42 g, 6.86 mmol) in THF (25 mL). The resulting pale yellow solution was stirred at −78° C. for 15 minutes, then a solution of 3-formyl-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester (1.60 g, 6.86 mmol) in THF (5 mL) was then slowly added. The reaction mixture was stirred at −78° C. for 30 minutes and then warmed to room temperature over a period of 1 hour. The reaction was quenched by addition of a saturated aqueous solution of NH4Cl and diluted with water. The resulting mixture was extracted with EtOAc, and the combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (10% to 50% of EtOAc in hexane) to give 1.76 g (51% yield) of 3-[hydroxy-(1-triisopropylsilanyl-1H-indol-5-yl)-methyl]-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester as a white foamy solid.

후처리

  1. stirringThe reaction mixture was stirred at −78° C. for 30 minutes
  2. temperaturewarmed to room temperature over a period of 1 hour
  3. customThe reaction was quenched by addition of a saturated aqueous solution of NH4Cl
  4. additiondiluted with water
  5. extractionThe resulting mixture was extracted with EtOAc
  6. dry with materialthe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash chromatography (10% to 50% of EtOAc in hexane)

출처 및 근거

ORD 기록
ord-c1113d0a01a046f38a7c5253fcdc33c5
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513425B2

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