Tert-Butanesulfinamide → HCID 178455589, compound

Participants

Reaction Steps

To a solution of cis-3-(tert-butyldimethylsilanyloxy)-cyclobutanecarbaldehyde (crude from step 3, 900 mg, 4.2 mmol) and 2-methylpropane-2-sulfinamide (509 mg, 4.2 mmol) in dry CH2Cl2 (10 mL) was added anhydrous CuSO4 (1.47 g, 9.24 mmol). The heterogeneous reaction mixture was stirred at room temperature overnight then filtered over Celite, rinsing with CH2Cl2. The filtrate was absorbed onto SiO2 and purified via chromatography with 0% to 20% EtOAc/hexanes to isolate 642 mg (48%) of 2-methyl-propane-2-sulfinic acid 1-[cis-3-(tert-butyldimethylsilanyloxy)-cyclobutyl]-meth-(E)-ylideneamide as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.04 (d, J=5.3 Hz, 1H), 4.25 (quin, J=7.4 Hz, 1H), 2.73-2.88 (m, 1H), 2.46-2.59 (m, 2H), 2.06-2.18 (m, 2H), 1.19 (s, 9H), 0.89 (s, 9H), 0.05 (s, 6H).

Provenance & Evidence