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

HRID 1912521Notes

Reaction equation

CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]3[CH2:19][C@@H:14]2[C:15]3([CH3:21])[CH3:20])(=O)=O)=CC=1.[C-:22]#[N:23].[K+]>CS(C)=O.[Cl-].[Na+].O>[CH3:21][C:15]1([CH3:20])[C@H:14]2[CH2:19][C@@H:16]1[CH2:17][CH2:18][C@@H:13]2[CH2:12][C:22]#[N:23]

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

extractionextracted with ether (3×75 mL)
dry with materialThe organic extracts were dried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by flash chromatography on SiO2 (Hexanes/ethyl acetate, gradient 0 to 50%)

Sources & evidence

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

Reaction notes

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