tert-Butylsulfinamide, (R)-(+)- → (NE,R)-2-methyl-N-[[4-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamide

Participants

Reaction Steps

To a solution of 4-trifluoromethyl-pyridine-2-carbaldehyde (287 mg, 1.64 mmol) and (R)-2-methylpropane-2-sulfinamide (209 mg, 1.72 mmol) in CH2Cl2 (10 mL) was added anhydrous copper (II) sulfate (576 mg, 3.61 mmol). The reaction mixture was stirred at room temperature overnight then filtered over a Buchner funnel, rinsing with CH2Cl2. The filtrate was concentrated and the residue was absorbed on SiO2 and purified by chromatography with 20% to 40% EtOAc/hexanes to give 340 mg (75%) of (R)-2-methyl-propane-2-sulfinic acid 1-(4-trifluoromethyl-pyridin-2-yl)-meth-(E)-ylideneamide as a pale yellow oil.

Provenance & Evidence