Acetyl chloride → 3-Acetamidobicyclo[1.1.1]pentan-1-yl acetate

HRID 62617

反応式

HRID 62617 の反応式
[C:1]([O:4][C:5]12[CH2:9][C:7]([NH2:10])([CH2:8]1)[CH2:6]2)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].[C:16](Cl)(=[O:18])[CH3:17]>CN(C=O)C>[C:1]([O:4][C:5]12[CH2:9][C:7]([NH:10][C:16](=[O:18])[CH3:17])([CH2:8]1)[CH2:6]2)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 904111873-Aminobicyclo[1.1.1]pentan-1-yl acetate

生成物 1

HCID 862879553-Acetamidobicyclo[1.1.1]pentan-1-yl acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a DMF (2 mL) solution of 3-aminobicyclo[1.1.1]pentan-1-yl acetate (1 mmol) is added sodium bicarbonate (3 mmol) and then acetyl chloride (1 mmol) by syringe at 0° C. The reaction is allowed to warm up to r.t. and monitored by LCMS. After LCMS analysis indicated consumption of starting material, the reaction is diluted with water and extracted with EtOAc (3×). The organic layers are combined, washed with brine, dried (magnesium sulfate), filtered, and concentrated. The crude residue is subjected to flash chromatography (silica gel, EtOAc/hexanes) to give 3-acetamidobicyclo[1.1.1]pentan-1-yl acetate (3).

後処理

  1. customat 0° C
  2. customconsumption of starting material
  3. additionthe reaction is diluted with water
  4. extractionextracted with EtOAc (3×)
  5. washwashed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-2814188c3f934beb903b306c9d265374
出典データセット
uspto-grants-2016_09
特許番号
US09447026B2

関連ノート

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