METHOD OF OBTAINING (1S,5R)-6,6-DIMETHYLBICYCLO[3.1.1]HEPTANONE-2 ((-)-NOPINONE) Russian patent published in 2023 - IPC C07C45/27 C07C49/433 

FIELD: organic chemistry.

SUBSTANCE: invention relates to a method of the preparation of (1S,5R)-6,6-dimethylbicyclo[3.1.1]heptanone-2 ((-)-nopinone), used as an intermediate for the synthesis of chiral catalysts, disinfectants and antitumor drugs. The method of production of (-)-nopinone by oxidation of myrtenal with hydrogen peroxide (H₂O₂) is characterized by the following: the oxidation of myrtenal is carried out in DMF with “oxone” (2KHSO₅⋅KHSO₄⋅K₂SO₄) with stirring, molar ratio myrtenal:oxidizing agent 1:0.5–1.5, the mixture is stirred at room temperature until the starting aldehyde completely disappears, then the reaction mixture is diluted with water, the reaction products are extracted with ethyl acetate or diethyl ether, washed with water, MgSO ₄ is dried, the solvent is removed and the formate is hydrolyzed with a 5–10% alcohol solution of NaOH or KOH, at the end of the reaction the mixture is diluted with water, the products are extracted with ethyl acetate or diethyl ether, washed with water, a saturated NaCl solution, dried with magnesium sulfate and the solvent is removed.

EFFECT: simplified method of the synthesis of (-)-nopinone with a high yield of the target product.

1 cl, 1 tbl, 4 ex