Nitrogen → 3R-hydroxymyristic acid methyl ester

Temperature

50 °C

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.

1. additionThe reactor was charged with H2 (60 psi)
2. additionThe reactor was charged with H2 (60 psi)
3. temperatureThe reactor was cooled to room temperature
4. concentrationthe resulting orange solution was concentrated in vacuo
5. customThe residue was purified by silica gel chromatography (120 g RediSep column
6. washeluting with a gradient of 0% through 40% ethyl acetate/hexanes over 60 min

ORD record

ord-98d2328db0194ed29c1fe9adbdb51758

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722064B2