Potassium Cyanide → 2-((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)acetonitrile

https://huagongshe.com/reaction/1912521

Participants

Role	Name	HCID	Charge
Reactant	Potassium Cyanide	HCID 9032	—
Reactant	((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methyl 4-methylbenzenesulfonate	HCID 13213888	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	2-((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)acetonitrile	HCID 68751834	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of Example 21A (13.6 g, 44.2 mmol) in DMSO (100 mL) was added potassium cyanide (11.5 g, 177 mmol). The reaction was heated at 70° C. for 48 h. The mixture was diluted with brine and extracted with ether (3×75 mL). The organic extracts were dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography on SiO2 (Hexanes/ethyl acetate, gradient 0 to 50%) to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08609674B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-3f876f9d43a7405cba0bce28de4e418b
Source note	uspto-grants-2013_12