Butanal → (R)-2-(N-Phenyl-aminooxy)-butan-1-ol

HRID 500053

Reaktionsgleichung

Reaktionsgleichung von HRID 500053
N1CCC[C@H]1C(O)=O.[CH:9](=[O:13])[CH2:10][CH2:11][CH3:12].[N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].[BH4-].[Na+].P([O-])([O-])([O-])=O>C(#N)C.C(OCC)(=O)C.CO>[C:16]1([NH:14][O:15][C@H:10]([CH2:11][CH3:12])[CH2:9][OH:13])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

9

Edukt 5

HCID 261ButanalHCID 1061PhosphateHCID 11473NitrosobenzeneHCID 145742L-ProlineHCID 4311764Sodium borohydride

Produkt 1

HCID 11816230(R)-2-(N-Phenyl-aminooxy)-butan-1-olAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

At about −20° C., L-proline (4 g, 34.8 mmol) was added to solution of n-butyraldehyde (25 mL, 278 mmol) and nitrosobenzene (15 g, 140 mmol) in acetonitrile (300 mL). The mixture was stirred at about −20° C. for about 48 hours, methanol (50 mL) and sodium borohydride (16 g, 432 mmol) were added, the mixture was stirred for about 10 minutes, and phosphate buffer was added. Following standard extractive workup with ethyl acetate, the crude product was purified by column chromatography with silica gel (petroleum ether-ethyl acetate =5:1, v:v, elution) to afford the title product (10.8 g, 43%). 1H NMR (300 MHz, CDCl3) δ 7.30-7.25 (m, 2H), 7.01-6.96 (m, 3H), 3.90-3.74 (m, 3H), 1.75-1.57 (m, 2H), 1.02 (t, J=7.8 Hz, 3H); LC-MS: m/z=182 (M+H)+.

Aufarbeitung

  1. stirringthe mixture was stirred for about 10 minutes
  2. customthe crude product was purified by column chromatography with silica gel (petroleum ether-ethyl acetate =5:1, v:v, elution)

Quellen und Nachweise

ORD-Eintrag
ord-9c287d615b44465c8b90e329552ec1cf
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767860B2

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