3-[hydroxy-(1-triisopropylsilanyl-1H-indol-5-yl)-methyl]-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester → HCID 66688025、化合物

HRID 661530

反応式

HRID 661530 の反応式
[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH2:8][C:7]([CH:16]([OH:36])[C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:21]=[CH:20]3)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6]1)=[O:4]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH2:8][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([Si:26]([CH:30]([CH3:32])[CH3:31])([CH:33]([CH3:34])[CH3:35])[CH:27]([CH3:28])[CH3:29])[CH:21]=[CH:20]3)=[O:36])[CH2:6]1)=[O:4]

参加物

4

反応物 1

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

生成物 1

HCID 66688025HCID 66688025、化合物収率 109.5%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Manganese dioxide (85%, 256 mg, 2.95 mmol) was added to a solution of 3-[hydroxy-(1-triisopropylsilanyl-1H-indol-5-yl)-methyl]-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester (300 mg, 0.59 mmol) in toluene (8 mL). The reaction mixture was heated at 100° C. for 2 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was evaporated under reduced pressure to give 326 mg of 3-phenyl-3-(1-triisopropylsilanyl-1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid methyl ester as a colorless foamy oil. A portion of this product (298 mg, 0.59 mmol) was dissolved in THF (8 mL) and a solution of tetrabutylammonium fluoride (1.0 M in THF, 0.60 mL, 0.59 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes, then was quenched by addition of 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 (30% to 50% of EtOAc in hexane) to give 167 mg (81% 2 steps yield) of 3-(1H-indole-5-carbonyl)-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester as a white foam.

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a celite pad
  3. customThe filtrate was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-bc211daa86934e4ca1e80a6af2b89af7
出典データセット
uspto-grants-2011_12
特許番号
US08084623B2

関連ノート

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