Tetrahydrofuran → HCID 89827530, Verbindung

HRID 525354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525354
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20]1[CH2:24]OCC1.[CH2:25]([Mg]Br)[CH3:26].CCOC(C)=O>CCCCCC>[CH2:20]([C:10]([OH:12])([CH2:25][CH3:26])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:24]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10967413HCID 10967413, VerbindungHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 89827530HCID 89827530, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a two-necked 50 mL round bottom flask were added (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-phenylacetate (1.2 g, 5.68 mmol) and dry THF (30 mL). The resulting mixture was cooled to 0° C. Ethyl magnesium bromide (3.02 g, 22.72 mmol) (3M solution in diethyl ether) was added dropwise, and the mixture was slowly allowed to warm to ambient temperature. The mixture was then stirred at ambient temperature for 24 hours. After completion of reaction (monitored by TLC, TLC eluent: 30% EtOAc in hexane), the mixture was quenched in NH4Cl solution and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated to yield 1.2 g (90.0%) of (R)-tert-butyl (2-ethyl-2-hydroxy-1-phenylbutyl)carbamate as a white solid. 1H NMR (300 MHz, CDCl3) δ: 7.35-7.26 (m, 5H), 5.56 (d, J=9.1 Hz, 1H), 4.61 (d, J=9.4 Hz, 1H), 1.68-1.63 (m, 2H), 1.39 (s, 9H), 1.32-1.22 (m, 2H), 0.92 (t, J=7.4 Hz, 3H), 0.80 (t, J=7.4 Hz, 3H).

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. customthe mixture was quenched in NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-21867e90f3524476bdb49cd01e3f4b5e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340549B2

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