Tetrahydrofuran → N-{3-hydroxybicyclo[1.1.1]pentan-1-yl}acetamide

HRID 62606

반응식

HRID 62606 반응식
C1COCC1.C([O:9][C:10]12[CH2:14][C:12]([NH:15][C:16](=[O:18])[CH3:17])([CH2:13]1)[CH2:11]2)(=O)C.[OH-].[Na+]>CO>[OH:9][C:10]12[CH2:14][C:12]([NH:15][C:16](=[O:18])[CH3:17])([CH2:13]1)[CH2:11]2

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 862879553-Acetamidobicyclo[1.1.1]pentan-1-yl acetate

생성물 1

HCID 86287953N-{3-hydroxybicyclo[1.1.1]pentan-1-yl}acetamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a THF (2 mL) solution of 3-acetamidobicyclo[1.1.1]pentan-1-yl acetate (3) (1 mmol) is added methanol (0.7 mL) followed by a aqueous solution of NaOH (1.4 M, 0.7 mL, 1 eq) at room temperature. The mixture is stirred and monitored by TLC. After complete consumption of the starting material, saturated ammonium chloride is added and the mixture is stirred for 5 min. The volatiles are removed under vacuum and the resultant mixture is extracted with EtOAc (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 give N-(3-hydroxybicyclo[1.1.1]pentan-1-yl)acetamide (1).

후처리

  1. customAfter complete consumption of the starting material, saturated ammonium chloride
  2. additionis added
  3. stirringthe mixture is stirred for 5 min
  4. customThe volatiles are removed under vacuum
  5. extractionthe resultant mixture is extracted with EtOAc (3×)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e3a6ee10a94843b489eb9be554bfc059
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447025B2

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