Water → (1R,2S)-1'-(2-bromoethyl)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805334ノート

反応式

HRID 1805334 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]3=[O:19])[CH2:9]2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:30](Br)[CH2:31][Br:32].O>CN(C=O)C>[Br:32][CH2:31][CH2:30][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@:10]2([CH2:9][C@H:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:11]1=[O:19]

参加物

6

反応物 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

生成物 1

HCID 58305371(1R,2S)-1'-(2-bromoethyl)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one収率 41%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (173 mg, 0.64 m mol) in DMF (2 mL) was added KHMDS (0.5 M, 1.4 mL) dropwise at room temperature. The mixture was stirred for half an hour before adding ethylene dibromide (300 mg, 1.6 mmol). The mixture was warmed to 50° C. and stirred at that temperature for 14 hours. The mixture was poured into water, extracted with ethyl acetate (3×15 mL), dried and concentrated under reduced pressure. The residue was purified by flash column chromatography (gradient elution, 5-10% ethyl acetate in petroleum ether) to give the title compound as white solid (98 mg, 41%). LC/MS m/e calcd. for C18H15BrClNO: 375, observed (M+H)+: 376.

後処理

  1. stirringstirred at that temperature for 14 hours
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (gradient elution, 5-10% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-747f936876a84c258d7fb16c280ac833
出典データセット
uspto-grants-2013_01
特許番号
US08354443B2

反応ノート

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