Trimethylsilyl cyanide → N-(3-cyanooxetan-3-yl)-2-methylpropane-2-sulfinamide

To a yellow solution of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (1 g, 5.71 mmol) in CH2Cl2 (20 ml) in a 100 round-bottomed flask was added titanium tetraethoxide (0.651 g, 2.85 mmol) and the reaction mixture stirred for 10 min. TMSCN (1.530 ml, 11.41 mmol) was then added, and the resulting reaction mixture stirred at r.t. for overnight. The reaction mixture was poured into saturated brine solution, and then the suspension was filtered through a pad of Celite. The organic layer was separated, and the aqueous layer extracted with ethyl acetate (3×25 ml). The combined organic solution was washed with saturated brine solution, dried over Na2SO4, filtered and concentrated. The crude product was purified over neutral alumina column using 4% methanol in dichloromethane as eluent. Desired fractions were collected and concentrated to give the titled product as colorless oil (0.9 g, 78%).

1. customthe resulting reaction mixture
2. stirringstirred at r.t. for overnight
3. filtrationthe suspension was filtered through a pad of Celite
4. customThe organic layer was separated
5. extractionthe aqueous layer extracted with ethyl acetate (3×25 ml)
6. washThe combined organic solution was washed with saturated brine solution
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified over neutral alumina column
11. customDesired fractions were collected
12. concentrationconcentrated

ORD record

ord-a672e74ffe254174925e6f896f4cf956

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507683B2