Dimethylformamide → HCID 86761036, compound

Participants

Reaction Steps

Oxalyl chloride (65 μl, 0.77 mmol) was added to a suspension of (±)-cis-{1-[2,5-bis(trifluoromethyl)benzyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid (Example 56) (157 mg, 0.30 mmol) in DCM (10 ml). DMF (5 μl) was added and the pale yellow solution obtained was stirred at RT under N2, for 2 h. The yellow solution was concentrated in vacuo and oxalyl chloride removed by azeotroping with toluene to yield a yellow solid. This was dissolved in THF/MeCN (5 ml/5 ml) cooled to 0° C. and TMS diazomethane (0.3 ml, 2M in hexane, 0.60 mmol) was added under N2. The mixture was stirred for 5 h at 0° C. and then at RT for 16 h. The yellow solution was evaporated in vacuo to give a pale brown gum (164 mg). The crude product was purified by chromatography (silica, 10% EtOAc/isohexane) to give a clear gum (91 mg, 56%). M/Z (ES+) 488 (MH+).

Provenance & Evidence