HCID 86731810, compound → HCID 86731809, compound

Participants

Reaction Conditions

Reaction Steps

(1S,7R)-2,2-dimethyl-6-methylene-7-(3-oxobutyl)cycloheptanecarbaldehyde (11.8 g, 0.05 mol.), toluene (70.8 g, 600 wt. %) and (ethylenediamine)[1,2-bis(diphenylphosphino) ethane]ruthenium(bispivalate) (4.8 mg, 0.00625 mmol, 0.0125 mol.%) were loaded altogether in a 200 ml autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 50 bars hydrogen. It was then heated to 90° C. and hydrogen pressure was maintained to 30 bars during all the reaction to afford desired product with 92% selectivity. Upon reaction completion (checked by both hydrogen consumption and GC), autoclave was then cooled down to 25° C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and solvent was removed under vacuum. After flash chromatography, 4-((1R,2S)-2-(hydroxymethyl)-3,3-dimethyl-7-methylenecycloheptyl) butan-2-one was obtained in 85% yield.

Provenance & Evidence