Toluene → (2S,3R)-3-(3-Amino-phenyl)-1-(dimethylamino)-2-methyl-pentan-3-ol

HRID 1026783

Reaktionsgleichung

Reaktionsgleichung von HRID 1026783
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][N:6]([CH3:21])[CH2:7][C@H:8]([CH3:20])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=1)=[O:10].C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.[NH4+]>C1COCC1>[NH2:17][C:13]1[CH:12]=[C:11]([C@@:9]([OH:10])([CH2:1][CH3:2])[C@@H:8]([CH3:20])[CH2:7][N:6]([CH3:21])[CH3:5])[CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 24655Ammonium bisulfateHCID 53235125(S)-3-(dimethylamino)-2-methyl-1-(3-nitro-phenyl)-propan-1-oneHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 70664504(2S,3R)-3-(3-Amino-phenyl)-1-(dimethylamino)-2-methyl-pentan-3-olAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

726 ml of ethylmagnesium bromide (1M in THF; 0.726 mol) are added under a nitrogen flow into a 2-liter four-neck flask, provided with mechanical stirrer, thermometer and dropping funnel. A solution of (S)-3-(dimethylamino)-2-methyl-1-(3-nitro-phenyl)-propan-1-one (50 g, 0.242 mol) in 50 ml of THF are dripped maintaining the temperature between 15-30° C. The reaction is stirred at room temperature for 3 hours. It is cooled to about 10° C. and toluene (200 ml) and slowly a 20% ammonium hydrogen sulphate solution (200 ml) are added. The mixture is stirred for 30 minutes and the phases are separated after about 15 minutes of rest. The organic phase is concentrated under vacuum almost to oily residue. Then toluene (200 ml), 30% sodium metabisulfite solution (300 ml) are added. The mixture is stirred for 30 minutes and the phases are separated after about 15 minutes of rest. The aqueous phase is washed 2 times with 200 ml of toluene. The organic phases are eliminated while Cert-butylmethylether (200 ml) is added to the aqueous phase. The pH of the mixture is brought to 11-12 with 28% sodium hydroxide. The mixture is stirred for 30 minutes and the phases are separated after about 15 minutes of rest. The aqueous phase is eliminated while the organic phase is concentrated under vacuum to oily residue which solidifies by cooling. 35 g of a yellowish solid with a 95% HPLC purity are obtained.

Aufarbeitung

  1. customprovided with mechanical stirrer
  2. temperatureIt is cooled to about 10° C.
  3. stirringThe mixture is stirred for 30 minutes
  4. customthe phases are separated after about 15 minutes of rest
  5. concentrationThe organic phase is concentrated under vacuum almost to oily residue
  6. additionThen toluene (200 ml), 30% sodium metabisulfite solution (300 ml) are added
  7. stirringThe mixture is stirred for 30 minutes
  8. customthe phases are separated after about 15 minutes of rest
  9. washThe aqueous phase is washed 2 times with 200 ml of toluene
  10. additionis added to the aqueous phase
  11. stirringThe mixture is stirred for 30 minutes
  12. customthe phases are separated after about 15 minutes of rest
  13. concentrationis concentrated under vacuum to oily residue which
  14. temperatureby cooling

Quellen und Nachweise

ORD-Eintrag
ord-2be645676eda4e9e9986508764467296
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729308B2

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