Isobutyl iodide → 3-(2-Methylpropyl)pyrrolidin-2-one

HRID 727537노트

반응식

HRID 727537 반응식
[Li+].CC([N-]C(C)C)C.C[Si](C)(C)[N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].I[CH2:20][CH:21]([CH3:23])[CH3:22]>C1COCC1>[CH3:20][CH:21]([CH3:23])[CH2:22][CH:13]1[CH2:14][CH2:15][NH:11][C:12]1=[O:16]

참가 물질

5

반응물 3

HCID 10556Isobutyl iodideHCID 844611-(Trimethylsilyl)pyrrolidin-2-oneHCID 2724682Lithium diisopropylamide

생성물 1

HCID 184426853-(2-Methylpropyl)pyrrolidin-2-one수율 41%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

A solution of LDA (2.0M, 111 mL, 222 mmol) and THF (300 mL) is cooled to -78° C. and a solution of 1-trimethylsilyl-2-pyrrolidinone (29.4 g, 221 mmol) in THF (145 mL) is added. After stirring for 45 minutes at -78° C., the enolate solution is added via cannula over 1 hour to a solution of 1-iodo-2-methylpropane (42.7 g, 232 mmol) in THF (200 mL) at -78° C. The solution is allowed to warm slowly and stirred at room temperature overnight. The reaction is quenched by the addition of 50 mL of acetic acid. Aqueous workup (EtOAc, MgSO4) and purification by column chromatography (30→100% EtOAc/hexane) gives 12.8 g of the title compound as an oil.

후처리

  1. temperatureto warm slowly
  2. stirringstirred at room temperature overnight
  3. customThe reaction is quenched by the addition of 50 mL of acetic acid
  4. customAqueous workup (EtOAc, MgSO4) and purification by column chromatography (30→100% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-5487c2c6c2834ee09d2a631091ed38c5
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712300

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