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

HRID 62606

Reaction equation

HRID 62606 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e3a6ee10a94843b489eb9be554bfc059
Source dataset
uspto-grants-2016_09
Patent number
US09447025B2

Linked notes

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