(R)-beta-aminophenethyl alcohol → HCID 90025824, Verbindung

HRID 59690

Reaktionsgleichung

[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([O:5]N1C(=O)CCC1=O)=O.[CH:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([NH2:31])[CH2:29][OH:30])=[CH:24][CH:23]=1>C1COCC1>[OH:30][CH2:29][C@H:28]([NH:31][C:3](=[O:5])[C@@H:2]([CH3:1])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 48 °C

Versuchsvorschrift

To a solution consisting of (±)-2,5-dioxopyrrolidin-1-yl 2-methyl-5-phenyl pentanoate (18mb(i), 85.6 g, 296 mmol) in THF (3000 mL) at 48° C. was added R-(−)-2-phenylglycinol (65.9 g, 480 mmol, Bridge Organics) in portions. The resulting reaction mixture was stirred at 48° C. for 40 hours. A white precipitate formed, which was filtered from the reaction mixture and washed with THF. The filtrate was concentrated under vacuum and the residue, comprising the diastereomeric pair, was chromatographed on silica gel. Elution with ethyl acetate-heptane (50:50 v/v) afforded the pure diastereomer title compound (31.3 g, 34%) as a colorless solid; TLC Rf 0.205 (solvent system: 50:50 v/v ethyl acetate-heptane); HPLC retention time 15.1 minutes, stationary phase: Gemini 5μ C18 250×4.6 mm, ultraviolet detector at 210 nm, mobile phase: 1 mL/min, 60:40:0.1 v/v methanol-water-acetic acid.

Aufarbeitung

customThe resulting reaction mixture
customA white precipitate formed
filtrationwhich was filtered from the reaction mixture
washwashed with THF
concentrationThe filtrate was concentrated under vacuum
customwas chromatographed on silica gel
washElution with ethyl acetate-heptane (50:50 v/v)

Quellen und Nachweise

ORD-Eintrag: ord-845b5e6a71054bcaa8d4933eb583801c
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09440919B2

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