2-Butene, 1-bromo-3-methyl- → HCID 18922258、化合物

HRID 743463ノート

反応式

HRID 743463 の反応式
[Li+].CC([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:22])[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:14].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>C1COCC1>[CH3:9][O:10][C:11](=[O:22])[CH:12]([CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH3:14]

参加物

5

反応物 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 2724682Lithium diisopropylamideHCID 14018930Methyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

生成物 1

HCID 18922258HCID 18922258、化合物収率 63.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A 2 M solution of LDA (70.32 ml, 0.14 mol) was added (via syringe) to a solution of N-t-butoxycarbonyl-sarcosine methyl ester (26 g, 0.1279 mol) in 40 ml of dry THF at -78° C. under nitrogen and the mixture was stirred at this temperature for 30 minutes. To the above mixture was added 4-bromo-2-methyl-2-butene (20 g, 0.134 mol) with stirring continuing at -78° C., and the resulting mixture was allowed to warm to room temperature. The reaction mixture was quenched with 6 ml of saturated ammonium chloride solution at -78° C., 20 ml of water added, and the resulting reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo to yield a yellow oil, which was purified by silica gel column chromatography (20% ethyl acetate in hexane) to afford 22.1 g (63.7 %) of N-t-butoxycarbonyl-2-(3-methyl-2-butenyl)-sarcosine methyl ester as an oil.

後処理

  1. stirringwith stirring
  2. customcontinuing at -78° C.
  3. customThe reaction mixture was quenched with 6 ml of saturated ammonium chloride solution at -78° C.
  4. addition20 ml of water added
  5. customthe resulting reaction mixture
  6. extractionwas extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto yield a yellow oil, which
  11. customwas purified by silica gel column chromatography (20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-4bad613defb3489ba9fbc7e755afd53e
出典データセット
uspto-grants-1996_09
特許番号
US05556909

反応ノート

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