Hydrochloric Acid → (2R)-3-Phenylpropane-1,2-diamine

HRID 351340

Reaktionsgleichung

Reaktionsgleichung von HRID 351340
[NH2:1][C@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]#[N:4].Cl.[H][H].N[C@H](CC1C=CC=CC=1)CO>CO.O.[Pd]>[C:6]1([CH2:5][C@@H:2]([NH2:1])[CH2:3][NH2:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 853475phenylalaninol, (R)-HCID 12113026(2R)-2-Amino-3-phenylpropanenitrileHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 12699299(2R)-3-Phenylpropane-1,2-diamineAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 9.0 g (49 mmol) of (R)-2-amino-3-phenylpropionitrile.HCl-salt (97.5% e.e.) in 280 mL of methanol-water 1:1 was added 2.2 equiv. of conc. HCl solution and 2.0 g of 5% Pd/C. The solution was hydrogenated for 19 h at 35° C. and 0.9 MPa of hydrogen pressure. Then additional 2 g of Pd/C was added and hydrogenation was continued for 24 h at 3.0 MPa. According to chiral HPLC 91% of (R)-2-amino-3-phenyl-1-propanol was formed together with 6% of (R)-3-phenyl-1,2-diaminopropane The reaction mixture was filtered and partially evaporated. The solution was basified to pH 10 using diluted NaOH solution and extracted with CH2CL2. The organic solution was dried over Na2SO4 and evaporated.

Aufarbeitung

  1. waithydrogenation was continued for 24 h at 3.0 MPa

Quellen und Nachweise

ORD-Eintrag
ord-7098506dc436431584fa78b5060cb395
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183443B2

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