methyl (S)-3-hydroxyheptanoate → 3-Fluoroheptanoic acid

Participants

Reaction Steps

Incidentally, methyl (R)-3-fluoroheptanoate derived from methyl (S)-3-hydroxyheptanoate (98.8%ee, [α]D20 =9.07) was hydrolyzed to obtain 3-fluoroheptanoic acid, which was then reacted with R-(+)-1-(1-naphthyl)ethylamine to form a diastereomer. The resulting diastereomer was found to have an optical purity of 98.7%ee by liquid chromatography, indicating that no racemization took place at all. NMR (ppm): 0.92 (3H, t, J=7.2 Hz), 1.36 (4H, m), 1.66 (2H, m), 2.62 (2H, m), 3.72 (3H, s), 4.93 (1H, m)

Provenance & Evidence