Ethanol → (1S)-1-phenylethanaminium

HRID 2371

Reaktionsgleichung

Reaktionsgleichung von HRID 2371
[CH:1](O)([C:7](O)=O)[CH:2](O)[C:3]([OH:5])=[O:4].[C:11]1([C@@H:17]([NH2:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([OH:22])C>>[OH:22][C@@H:17]1[CH2:18][CH2:7][C@H:1]([CH2:2][C:3]([O-:5])=[O:4])[C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:11]1([C@@H:17]([NH3+:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH:22][C@@H:17]1[CH2:18][CH2:7][C@H:1]([CH2:2][C:3]([OH:5])=[O:4])[C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

6

Edukt 3

HCID 702Ethanol2×HCID 8752,3-Dihydroxybutanedioic AcidHCID 758181-Phenethylamine, (-)-

Produkt 3

HCID 7855572(1S)-1-phenylethanaminiumHCID 11171909(+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acidHCID 131720568(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

Versuchsvorschrift

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).

Quellen und Nachweise

ORD-Eintrag
ord-9351ff791ece43d89068d7c5e43ad1d4
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728866

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