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

HRID 62605노트

반응식

HRID 62605 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 room temperature 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).

후처리

  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

출처 및 근거

ORD 기록
ord-e13f7f00e4374bfd90fc6ea29253b12a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447025B2

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