tert-Butylsulfinamide, (R)-(+)- → HCID 178434549, compound

Participants

Reaction Conditions

Reaction Steps

3-methyl-1H-pyrazole-4-carbaldehyde (2.03 g, 18.44 mmol) was dissolved in THF (30 ml) and (R)-2-methylpropane-2-sulfinamide (2.35, 19.39 mmol) was added followed by Ti(OEt)4 (8.41 mmol, 36.90 mmol). The resulting reaction mixture was stirred at 80° C. for 18 h. LCMS shows mostly product. The reaction mixture was diluted with EtOAc (300 mL), washed with 4% aqueous NaCl (2×150, 2×50 mL). The combined aq. layers were back extracted with EtOAc (100 ml). The combined organic layers were washed with brine (100 ml), dried over Na2SO4, filtered and concentrated. Purified by column chromatography (REDI 80 g, EtOAc/heptane 20-100% over 33 min 100% for 7 min.) to give title compound (2.25 g, 10.55 mmol).

Provenance & Evidence