Dimethylamine → Ethyl 1-[(dimethylamino)methyl]cyclopropanecarboxylate

HRID 34123Notes

Reaction equation

HRID 34123 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:9]OS(C)(=O)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:15][NH:16][CH3:17]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1([CH2:9][N:16]([CH3:17])[CH3:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 574666101-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 60034732Ethyl 1-[(dimethylamino)methyl]cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 222 mg of 1-methanesulfonyloxymethyl-cyclopropane carboxylic acid ethyl ester in 5 mL of tetrahydrofuran was added 3 mL of 2M dimethyl amine in tetrahydrofuran, and stirred at room temperature for 3 days. The solvent was distilled off, and the residue was added with 2 mL of 1N hydrochloric acid, and washed with diethyl ether. The aqueous layer was added with 10% potassium carbonate aqueous solution, and extracted with ethyl acetate. The extracted layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 56 mg of the title compound as a pale yellow oil.

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was added with 2 mL of 1N hydrochloric acid
  3. washwashed with diethyl ether
  4. additionThe aqueous layer was added with 10% potassium carbonate aqueous solution
  5. extractionextracted with ethyl acetate
  6. washThe extracted layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-864b41905396449fbae3ee8dca74fb67
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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