Dicyclohexylcarbodiimide → N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropane-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

Trifluoromethyl cyclopropane carboxylic acid (500 mg, 3.24 mmol) was added to a freshly prepared solution of Weinreb amine (3.90 mmol) prepared by treating N-methoxymethanamine HCl salt with EtN-iPr2 (3.90 mmol) in CH2Cl2 at −40° C. and stirring for 5 min. DCC (801 mg, 3.90 mmol) in 5.0 mL of DCM was then added slowly over 3 min while cooling the solution at 0° C. The reaction mixture was stirred at RT for 48 h. It was then filtered through a plug of silica gel washing with Et2O. The volatiles were removed and the residue was purified on an ISCO 12 g column (20-70% EtOAc:Hexanes) to yield N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropanecarboxamide (456 mg, 71% yield) as a clear colorless oil. A reference for this procedure could be found in: J. Org. Chem. 2005, 70, pages 5721-5724.

Provenance & Evidence