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

HRID 727537ノート

反応式

HRID 727537 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 184426853-(2-Methylpropyl)pyrrolidin-2-one収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5487c2c6c2834ee09d2a631091ed38c5
出典データセット
uspto-grants-1998_01
特許番号
US05712300

反応ノート

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