(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile → (R)-2-amino-6-((1-butyrylpiperidin-2-yl)methoxy)benzonitrile

HRID 1483957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483957
[C:1]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[C:15]=1[C:16]#[N:17])(=[O:5])[CH2:2][CH2:3][CH3:4].[H][H]>C(O)C.[Pd]>[NH2:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH2:12][C@H:7]2[CH2:8][CH2:9][CH2:10][CH2:11][N:6]2[C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[C:15]=1[C:16]#[N:17]

Komponenten

5

Edukt 2

HCID 86714289(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrileHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86714288(R)-2-amino-6-((1-butyrylpiperidin-2-yl)methoxy)benzonitrileAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile (Example 16b, 1.5 g, 4.53 mmol) in ethanol (40 mL) was added 10% Pd/C (300 mg). The reaction mixture was charged with hydrogen balloon at room temperature overnight then then filtered through celite and concentrated under reduced pressure. The residue was purified by Biotage SP-1 (40s column) eluting with EtOAc/Hexane (10%-70%) to give the desired product as an oil (1.1 g, 81%). H NMR (400 MHz, DMSO-d6) δ 0.86 (t, J=7.2 Hz, 3H), 1.46-1.65 (m, 7H), 1.77-1.85 (m, 1H), 2.24-2.30 (m, 1H), 2.38-2.42 (m, 1H), 2.56-2.63 (m, 0.5H), 3.1-3.16 (m, 0.5H), 3.71-3.74 (m, 0.3H), 3.92-3.98 (m, 1H), y 2H), 7.15-7.19 (m, 1H). MS 302 (MH+).

Aufarbeitung

  1. filtrationfiltered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by Biotage SP-1 (40s column)
  4. washeluting with EtOAc/Hexane (10%-70%)

Quellen und Nachweise

ORD-Eintrag
ord-7603722a443a481ba7e647cba3d840c6
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09420814B2

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