1-Benzyl-3-nitro-4-phenylpyrrolidine → 1-Benzyl-4-phenylpyrrolidin-3-amine

HRID 590779

Reaktionsgleichung

Reaktionsgleichung von HRID 590779
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([N+:19]([O-])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N.[Ni]>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([NH2:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 580091801-Benzyl-3-nitro-4-phenylpyrrolidine

Produkt 1

HCID 433170851-Benzyl-4-phenylpyrrolidin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittel

Versuchsvorschrift

To a stirred solution of (3S and R, 4R and S)-1-benzyl-3-nitro-4-phenylpyrrolidine (100 g, 0.354 mol) in methanolic ammonia (1 L) was added Raney Ni (20 g) at room temperature in a 2.0 L hydrogenation flask. The reaction was hydrogenated at 100 psi for 12 h at room temperature. After completion of the reaction, the mixture was filtered through Celite and the filtrate was concentrated in vacuo to afford (3S and R, 4R and S)-1-benzyl-4-phenylpyrrolidin-3-amine, which was carried onto the next step without further purification. MS ESI calc'd. For C17H20N2 [M+1]+ 253. found 253.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-68b8356b995d4c9ebc366b7069a56724
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233979B2

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