Dimethyl Sulfoxide → HCID 77230831, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (15.44 ml, 2 M in DCM, 30.9 mmol) in DCM (100 ml) was added DMSO (4.38 ml, 61.8 mmol) at −78° C. The mixture was stirred at −78° C. for 5 min. Followed by the addition of tert-butyl-5-(hydroxymethyl)-2-phenylpiperidine-1-carboxylate (3.6 g, 12.35 mmol) in DCM (10 mL). The resulting mixture was stirred at −78° C. for 15 min, then triethyl amine (13.78 ml, 99 mmol) was added. The mixture was warmed up to 0° C., quenched with NH4Cl aqueous, and diluted with ether. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting crude product was directly used in the next step.

Provenance & Evidence