Ethyl Acetate → 1-{3-Aminobicyclo[1.1.1]pentan-1-yl}ethan-1-one

HRID 62615Notes

Reaction equation

HRID 62615 reaction equation
[NH2:1][C:2]12[CH2:6][C:4]([C:7]([OH:9])=O)([CH2:5]1)[CH2:3]2.C[Li].[Cl-].[NH4+].[C:14](OCC)(=O)C>C1COCC1>[NH2:1][C:2]12[CH2:3][C:4]([C:7](=[O:9])[CH3:14])([CH2:5]1)[CH2:6]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 253246613-Aminobicyclo(1.1.1)pentane-1-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 904108111-{3-Aminobicyclo[1.1.1]pentan-1-yl}ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-aminobicyclo[1.1.1]pentane-1-carboxylic acid (1 mmol) in anhydrous THF (2 mL) at 0° C. under nitrogen is added a methyllithium (1.4 M in diethyl ether, 4 mmol) in a dropwise manner. After addition, the reaction mixture is slowly allowed to warm to room temperature (r.t.), stirred overnight, and treated with aqueous saturated ammonium chloride solution (4 mL). Ethyl acetate (2 mL) is added and organic layer are separated. The aqueous layer is extracted with ethyl acetate (3×1 mL). The combined organic layers are dried (Mg2SO4) and concentrated. The residue is purified by a flash chromatography on silica gel (EtOAc/hexanes) to give 1-(3-aminobicyclo[1.1.1]pentan-1-yl)ethanone.

Workup

  1. additionAfter addition
  2. customorganic layer are separated
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×1 mL)
  4. dry with materialThe combined organic layers are dried (Mg2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by a flash chromatography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-2a6f5e3f0b0442759f3fd669807d73a4
Source dataset
uspto-grants-2016_09
Patent number
US09447026B2

Reaction notes

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