Nitrogen → 3R-hydroxymyristic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A slurry of methyl 3-oxotetradecanoate (29, 29.0 g, 113 mmol) in methanol (120 mL) was purged in a 300 mL high pressure reactor glass sleeve with N2 for 10 minutes. Dichloro-R-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ruthenium (897 mg, 1.10 mmol) was added. The mixture was placed in a Parr 5500 series compact reactor. The reactor was charged with H2 (60 psi) and vented 3 times. The reactor was charged with H2 (60 psi) and stirred (1200 rpm) and heated to 50° C. for 20 h. The reactor was cooled to room temperature, and the resulting orange solution was concentrated in vacuo. The residue was purified by silica gel chromatography (120 g RediSep column, eluting with a gradient of 0% through 40% ethyl acetate/hexanes over 60 min, 85 mL/min) to provide product 30 (28.5 g, 97% yield) as a white solid.

Provenance & Evidence