Trimethylaluminum → N-(2-cyclopropylpropan-2-yl)-2-methylpropane-2-sulfinamide

Temperature

-78 °C

To a stirred solution of (E)-N-(1-cyclopropylethylidene)-2-methylpropane-2-sulfinamide (0.6 g, 3.2 mmol) in 30 mL of toluene at −78° C. was added Me3Al (1.76 mL, 3.5 mmol, 2M in toluene) under nitrogen atmosphere. After stirred 20 minutes at −78° C., MeLi (2.3 mL, 7 mmol, 3M in dimethoxymethane) was added drop-wise and the mixture stirred at −78° C. for 4 hours. The reaction was quenched by adding 2 mL of water. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (4:1, v/v) to give N-(2-cyclopropylpropan-2-yl)-2-methylpropane-2-sulfinamide (0.18 g, 28%) as a yellow oil. MS: (M+H)+=204.1; 1H NMR (300 MHz, CDCl3): δ 3.03 (brs, 1H), 1.17 (s, 3H), 1.16 (s, 9H), 1.12 (s, 3H), 0.98-0.95 (m, 1H), 0.43-0.29 (m, 4H).

1. stirringthe mixture stirred at −78° C. for 4 hours
2. customThe reaction was quenched
3. additionby adding 2 mL of water
4. customThe solvent was removed under reduced pressure
5. customthe residue was purified by column chromatography (silica gel, 200-300 mesh
6. washeluting with a mixture of petroleum ether and ethyl acetate (4:1

ORD record

ord-673e011056514a2d9fdfce9ba540ae6b

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2