Iodoethane → N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

HRID 62607

反応式

HRID 62607 の反応式
[OH:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2.[H-].[Na+].I[CH2:14][CH3:15]>C1COCC1>[CH2:14]([O:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2)[CH3:15]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86287953N-{3-hydroxybicyclo[1.1.1]pentan-1-yl}acetamide

生成物 1

HCID 86287954N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a anhydrous THF (5 mL) solution of N-(3-hydroxybicyclo[1.1.1]pentan-1-yl)acetamide (1) (1 mmol) is added NaH (60% dispersion in mineral oil, 3 mmol) portionwise at 0° C. After addition, the mixture is stirred until the evolution of gas stops. Iodoethane (1 mmol) is then added by syringe slowly. The reaction is monitored by LCMS and TLC. After consumption of starting material, the reaction mixture is quenched by adding water (3 mL) and extracted with ethyl acetate (3×). The organic layers are combined, dried (magnesium sulfate), filtered, and concentrated. The crude residue is subjected to flash chromatography (silica gel, EtOAc/hexanes) to afford N-(3-ethoxybicyclo[1.1.1]pentan-1-yl)acetamide (2).

後処理

  1. additionAfter addition
  2. customAfter consumption of starting material
  3. customthe reaction mixture is quenched
  4. additionby adding water (3 mL)
  5. extractionextracted with ethyl acetate (3×)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-7041294fee3745909557675e4ea95d88
出典データセット
uspto-grants-2016_09
特許番号
US09447025B2

関連ノート

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