Ethanolamine → HCID 57699419, Verbindung

HRID 77293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77293
[CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:7]=[C:8]([C@@H:13]2[CH2:15][O:14]2)[CH:9]=[CH:10][C:11]=1[Cl:12]>C(O)(C)C>[Cl:5][C:6]1[CH:7]=[C:8]([C@@H:13]([OH:14])[CH2:15][NH:4][CH2:3][CH2:1][OH:2])[CH:9]=[CH:10][C:11]=1[Cl:12]

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 10352473(2R)-2-(3,4-dichlorophenyl)oxirane

Produkt 1

HCID 57699419HCID 57699419, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

In a 3 neck flask equipped with a mechanical stirrer, thermocouple and addition funnel in an ambient temperature water bath was added ethanolamine (330 mL, 5.47 mol). (R)-2-(3,4-dichlorophenyl)oxirane (184 g, 976 mmol) in isopropanol (75 mL) was added dropwise over 1 h. Reaction temperature stayed <30° C. during addition. The reaction mixture was stirred at ambient temperature for 14 h, diluted with 2000 mL of ice water and extracted three times with 1000 mL of ethyl acetate. The combined organic phases were dried over MgSO4, filtered over Celite and concentrated in vacuo affording (1R)-1-(3,4-dichlorophenyl)-2-(2-hydroxyethylamino)-ethanol (244 g, 100%) as a white semi-solid. 1H-NMR (400 MHz, CDCl3) δ 7.58-7.54 (m, 2H), 7.35-7.32 (m, 1H), 5.51 (s, 1H), 4.64 (dd, J=5.0, 7.2 Hz, 1H), 4.49 (s, 1H), 3.43 (dd, J=5.0, 10.4 Hz, 2H), 2.69-2.50 (m, 4H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=250.3; tR=0.84 min.

Aufarbeitung

  1. customIn a 3 neck flask equipped with a mechanical stirrer
  2. additionthermocouple and addition funnel in an ambient temperature water bath
  3. customReaction temperature
  4. additionstayed <30° C. during addition
  5. extractionextracted three times with 1000 mL of ethyl acetate
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered over Celite
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6694b905d3e14b5f8b6ac339eb25d977
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841282B2

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