Methanol → HCID 53432669, compound

Participants

Reaction Conditions

Reaction Steps

A glass liner is charged with ethyl 3-cyano-5-methylhex-3-enoate (starting material prepared above), methanol (100 mL), and water (18 mL). Potassium hydroxide is added with stirring. A liner is placed in a 600 mL PARR hydrogenation vessel. The vessel is purged with nitrogen and then with hydrogen via charging to 60 psi and releasing the pressure on 5 cycles. The vessel is heated to 55° C. A solution of [(R,R)-MeDuPHOS]Rh(COD)+BF4− in deoxygenated methanol (18.0 mg in 20 mL) is added via syringe. The vessel is again purged with hydrogen and then pressurized to 60 psi with stirring. Periodically, hydrogen is added to maintain the pressure between 50 to 60 psi. Hydrogen uptake ceases after 5 hours. After an additional 1 hour, the mixture is cooled to room temperature, and the pressure is released. The mixture is transferred to a flask, and the solvent is removed in vacuo to give the product. A small sample is removed and converted to (S)-3-cyano-5-methylhexanoic acid by reaction with 1N hydrochloric acid. GC analysis shows 98.7% conversion to the desired cyano alkanoic salt with 96.6% e.e S isomer.

Provenance & Evidence