Oxalyl chloride → 3-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionyl chloride

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionic acid (prepared as in Example 79, 210 mg, 0.73 mmol) was dissolved in methylene chloride (10 mL) and N,N-dimethylfomamide (one drop) and cooled to 0° C. To this solution was added dropwise a solution of oxalyl chloride in methylene chloride (2 M solution, 421 μL, 0.84 mmol) which produced gas evolution and it was then warmed to 25° C. and stirred for 1 h. After this time, the reaction was concentrated in vacuo to about 1.5 mL and then enough methylene chloride was added to bring the total volume to 6 mL. This resulted in a roughly 0.12 M solution of 3-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionyl chloride which was used crude without purification.

Provenance & Evidence