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

HRID 2209373Notes

Reaction equation

HRID 2209373 reaction equation
[F:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6]C)=[O:5].O[C@@H](CCCC)CC(OC)=O>>[F:1][CH:2]([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 10419468methyl (S)-3-hydroxyheptanoateHCID 54466993methyl (R)-3-fluoroheptanoate

Product 1

HCID 193806173-Fluoroheptanoic acid

Procedure

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)

Sources & evidence

ORD record
ord-569ee12f5ee0413abfbb056b988123e2
Source dataset
uspto-grants-1995_10
Patent number
US05454976

Reaction notes

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