HCID 86708686, Verbindung → HCID 86708687, Verbindung

HRID 1430970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430970
[Cl:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][C:18]([C:24]#[N:25])=[CH:17][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1>CO.[Pd]>[NH2:21][C:20]1[C:2]([Cl:1])=[C:3]([CH:17]=[C:18]([C:24]#[N:25])[CH:19]=1)[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1

Komponenten

4

Edukt 1

HCID 86708686HCID 86708686, Verbindung

Produkt 1

HCID 86708687HCID 86708687, VerbindungAusbeute 18,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of (+/−)-tert-butyl 3-(2-chloro-5-cyano-3-nitrophenoxy)pyrrolidine-1-carboxylate (278 mg, 0.756 mmol) and Pd/C (80 mg, 0.038 mmol) in Methanol (20 mL) was hydrogenated at 20 psi for 2 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 5-60% ethyl acetate/hexanes) to give (+/−)-tert-butyl 3-(3-amino-2-chloro-5-cyanophenoxy)pyrrolidine-1-carboxylate (48 mg).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (40 g column, eluting with 5-60% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6352c655c5734545baa6db26ae62d38a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940736B2

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