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

HRID 661529ノート

反応式

HRID 661529 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-68b97ab60d2540c1b9ef911713a6015f
出典データセット
uspto-grants-2011_12
特許番号
US08084623B2

反応ノート

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