Methyl iodide → 3-(Methylamino)bicyclo[1.1.1]pentan-1-yl acetate

HRID 62608Notes

Reaction equation

HRID 62608 reaction equation
[C:1]([O:4][C:5]12[CH2:9][C:7]([NH2:10])([CH2:8]1)[CH2:6]2)(=[O:3])[CH3:2].[C:11](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[C:1]([O:4][C:5]12[CH2:9][C:7]([NH:10][CH3:11])([CH2:8]1)[CH2:6]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 904111873-Aminobicyclo[1.1.1]pentan-1-yl acetate

Product 1

HCID 904109743-(Methylamino)bicyclo[1.1.1]pentan-1-yl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an anhydrous DMF (5 mL) solution of 3-aminobicyclo[1.1.1]pentan-1-yl acetate (1 mmol; prepared as described in Example 1, Step 2) is potassium carbonate (3 mmol) followed by the addition of methyl iodide (1 mmol) by syringe at room temperature. The reaction is monitored by LCMS and TLC. After consumption of starting material, the reaction mixture is quenched by adding water (3 mL) and extracted with ethyl acetate (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 afford 3-(methylamino)bicyclo[1.1.1]pentan-1-yl acetate.

Workup

  1. customAfter consumption of starting material
  2. customthe reaction mixture is quenched
  3. additionby adding water (3 mL)
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-442a741eeb5243b5a706c5e41e33d99f
Source dataset
uspto-grants-2016_09
Patent number
US09447025B2

Reaction notes

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