Ethyl 3-methyl-2-oxobutyrate → HCID 59843746, Verbindung

HRID 1666923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666923
[C:1]1([C@H:7]([CH2:9][OH:10])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][CH:12]([CH3:20])[C:13](=O)[C:14](OCC)=[O:15]>C(O)C(F)(F)F>[CH:12]([C:13]1[C:14](=[O:15])[O:10][CH2:9][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1)([CH3:20])[CH3:11]

Komponenten

4

Edukt 2

HCID 88406Ethyl 3-methyl-2-oxobutyrateHCID 2724025(R)-beta-aminophenethyl alcohol

Produkt 1

HCID 59843746HCID 59843746, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64092,2,2-TrifluoroethanolLösungsmittel

Versuchsvorschrift

(R)-2-phenylglycinol (4) (2.00 g, 14.6 mmol, 1.0 equiv.) and ethyl 3-methyl-2-oxobutyrate (2.20 mL, 14.6 mmol. 1.0 equiv.) were refluxed in trifluoroethanol (30 mL) over activated 4 molecular sieves (7.0 g) for 24 hours. Filtration through a short pad of CELITE® diatomaceous earth and removal of solvent from the filtrate in vacuo generated the crude product which was purified by flash column chromatography on silica, eluting with petrol and diethyl ether (4:1) to furnish the title compound as a colourless oil (1.13 g, 36%); v(max)(film) 2965 (C—H), 1740 (C═O), 1638 (C═N) cm−1; δH (250 MHz, CDCl3) 7.45-7.32 (5H, m, Ph), 4.90-4.83 (1H, m, PhCH), 4.55 (1H, dd, J 4.4 Hz, T 11.5 Hz, 6β-H), 4.13 (1H, dd/10.9 Hz, T 11.4 Hz, 6α-H), 3.32 (1H, m, CH(CH3)2), 1.25 (3H, d, J 5.0 Hz, CH(CH3)2×3), 1.22 (3H, d, /5.0 Hz, CH(CH3)2×3); δc (62.5 MHz, CDCl3) 167.7, 155.7, 137.5, 129.3, 128.6, 127.4, 71.7, 59.7, 32.7, 20.7, 19.9: m/z (CL, NH3), 220 (100%), 218 (MH+, 17%), 217 (27%), and 216 (25%); HRMS for C13H16NO2 requires 218.1177 found 218.1181. [α]D20 −207.5 (c 1.17 CHCl3).

Aufarbeitung

  1. customfor 24 hours
  2. filtrationFiltration
  3. customthrough a short pad of CELITE® diatomaceous earth and removal of solvent from the filtrate in vacuo
  4. customwas purified by flash column chromatography on silica
  5. washeluting with petrol and diethyl ether (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-a2b60c31502a47ad8946b79740612bf3
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044173B2

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