Réaction #2467

Équation de réaction

(-)-(S)-1-penylethylamine

ethanol

ethanol

racemic acid

→

(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

(S)-1-phenyl-ethylammonium

(+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid

Conditions de réaction

Mode opératoire

This acid presented the analytical characters of the racemic acid described under b) and a [α]20D =-12° (c=1.15, ethanol) (purity: 99%; e.r. 99.2:0.8). Proceeding in a manner analogous to that described here-above, but using (-)-(S)-1-penylethylamine (Fluka purum; e.r. 98:2), there was obtained (1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate of (S)-1-phenyl-ethylammonium (m.p. 131°-132°; [α]20D =+4°; c=1.05, ethanol) and (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid having [α]20D =+11° (c=1.10, ethanol) (purity: 99%; e.r. 96.5:3.5).

Source