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

HRID 1805334노트

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HRID 1805334 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-747f936876a84c258d7fb16c280ac833
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354443B2

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