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

HRID 1197387Notes

Reaction equation

HRID 1197387 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.

Sources & evidence

ORD record
ord-dad46dc236d144e6950b921db96c05fb
Source dataset
uspto-grants-1994_01
Patent number
US05275756

Reaction notes

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