Diethylamine → HCID 178465145, compound

Participants

Reaction Steps

A stirred and cooled (0° C.) solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (0.500 g, 2.69 mmol) in CH2Cl2 (10 mL) was treated dropwise with a solution of oxalyl chloride (2.0 M in CH2Cl2 1.58 mL, 3.15 mmol) and one drop of DMF, under an atmosphere of nitrogen. The reaction was stirred for 20 min at 0° C., allowed to warm to room temperature and stirred for an additional 2 h. The product was placed under high vacuo for 20 min, dissolved in THF (15 mL) and treated with diethylamine (2.0 M solution in THF, 1.37 mL, 2.73 mmol) and triethylamine (380 uL, 2.73 mmol). The reaction was stirred at room temperature for an additional 18 h. Saturated NH4Cl (1 mL) was added and the resultant mixture was partitioned between H2O (20 mL) and EtOAC (20 mL). The aqueous layer was re-extracted with EtOAc (3×20 mL) and the combined extracts were washed with brine (40 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford methyl trans-4-[(ethylamino)carbonyl]cyclohexanecarboxylate as a colorless oil. LCMS=214.2 (M+1)+.

Provenance & Evidence