Ammonium Acetate → HCID 10081308, Verbindung

HRID 1865316

Reaktionsgleichung

Reaktionsgleichung von HRID 1865316
O=[C:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.[NH4+:19]>CO>[NH2:19][C@H:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 517165Ammonium AcetateHCID 2760261Methyl 3-oxo-4-phenylbutanoate

Produkt 1

HCID 10081308HCID 10081308, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ru(OAc)2((R)-dm-binap) (0.248 g, 0.260 mmol), methyl 3-oxo-4-phenylbutanoate (10.00 g, 52.0 mmol), ammonium acetate (4.01 g, 52.0 mmol) and methanol (50 mL) were placed in a 200 mL stainless steel autoclave under nitrogen atmosphere, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was cooled down to room temperature and further stirred under a hydrogen pressure of 3 MPa at 80° C. for 14 hours. After completion of the reaction, the solvent was removed by evaporation to give methyl (3R)-3-amino-4-phenylbutanoate as a crude material (13.01 g). The enantiomeric excess of methyl (3R)-3-amino-4-phenylbutanoate in the crude product was determined to be 94.7% ee by HPLC analysis using a SUMICHIRAL OA-4100R column after conversion into methyl (3R)-3-(4-nitrobenzoylamino)-4-phenylbutanoate.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringfurther stirred under a hydrogen pressure of 3 MPa at 80° C. for 14 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-9e6686f33d584189b4ab82674c0cb643
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626034B2

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