Potassium tert-butoxide → 4-(Methoxymethyl)cyclohexanecarbonitrile

To a cold (−10° C.) solution of EXAMPLE 374C (1.18 g) and toluenesulfonylmethyl isocyanide (2.268 g) in dimethoxyethane (3 mL) and absolute ethanol (0.1 mL) was added (in small portions) potassium tert-butoxide (2.235 g). The reaction mixture was continued to stir at <5° C. for 30 minutes, warmed to room temperature, heated at 35° C. for 30 minutes and then at room temperature for 2 hours. The reaction mixture was concentrated and the residue was dissolved in water-brine, and extracted with dichloromethane. The dichloromethane layer was purified by flash chromatography, and was eluted with 5% ethyl acetate in dichloromethane to provide the title compound.

1. temperatureheated at 35° C. for 30 minutes
2. waitat room temperature for 2 hours
3. concentrationThe reaction mixture was concentrated
4. dissolutionthe residue was dissolved in water-brine
5. extractionextracted with dichloromethane
6. customThe dichloromethane layer was purified by flash chromatography
7. washwas eluted with 5% ethyl acetate in dichloromethane

ORD record

ord-49b10596bf6c48519497e071bc4119ff

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580794B2