Dicyclopropyl ketone → (R)-N-(dicyclopropylmethylidene)-2-methylpropane-2-sulfinamide

Temperature

150 °C

A 20-mL microwave vial containing a solution of dicyclopropyl ketone (0.778 ml, 6.81 mmol), (R)-2-methylpropane-2-sulfinamide (0.825 g, 6.81 mmol), and titanium ethoxide (1.427 ml, 6.81 mmol) in tetrahydrofuran (13.5 mL) under argon was heated in a microwave for 5 minutes at 150° C. and then again at 160° C. for an additional 5 minutes. The reaction mixture was poured into brine (14 mL), the resulting slurry filtered through Celite, and the two resulting layers were separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel flash chromatography (10-50% ethyl acetate/hexanes) to afford (R)—N-(dicyclopropylmethylidene)-2-methylpropane-2-sulfinamide (0.325 g, 1.52 mmol, 22% yield). MS ESI: [M+H]+ m/z 214.1.

1. filtrationthe resulting slurry filtered through Celite
2. customthe two resulting layers were separated
3. extractionThe aqueous layer was extracted with ethyl acetate
4. dry with materialthe combined organic layers were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude material was purified by silica gel flash chromatography (10-50% ethyl acetate/hexanes)

ORD record

ord-16849fc27c7c4977969e3eefe1a336d6

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759366B2