HCID 67263692, Verbindung → HCID 67264544, Verbindung

HRID 1687141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1687141
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[CH2:8][CH2:9][N:10]([CH2:13][C@H:14]([O:19][CH3:20])[C:15]([F:18])([F:17])[F:16])[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[F:18][C:15]([F:16])([F:17])[C@@H:14]([O:19][CH3:20])[CH2:13][N:10]1[CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([NH2:1])[CH:22]=[CH:21][C:7]=2[CH2:8][CH2:9]1

Komponenten

4

Edukt 1

HCID 67263692HCID 67263692, Verbindung

Produkt 1

HCID 67264544HCID 67264544, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

7-Nitro-3-((S)-3,3,3-trifluoro-2-methoxy-propyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (171 mg, 0.538 mmol, 1.0 eq) was placed in methanol (20 mL) and 10% palladium on carbon (17 mg) was added. The reaction was hydrogenated at 25 psi for 30 minutes. The mixture was then filtered through celite and concentrated under reduced pressure to obtain 3-((S)-3,3,3-trifluoro-2-methoxy-propyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine as a green amorphous solid (113 mg, 73%). LCMS (m/e) 289 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.89 (d, 1H, J=7.5 Hz), 6.51-6.45 (m, 2H), 3.76-3.66 (m, 1H), 3.61 (s, 3H), 3.63-3.52 (m, 2H), 2.88-2.79 (m, 6H), 2.78-2.69 (m, 4H).

Aufarbeitung

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d695ced8f3bb410994de209b526ff206
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

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