tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate → Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate

HRID 541216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541216
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:14][CH:15]=2)=[CH:5][CH:4]=1)#[N:2].C(C1C=CC(C2CCCN(C(OC(C)(C)C)=O)CC=2)=CC=1)#N>[Pd].C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 68288828tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate2×HCID 68288921tert-butyl 4-(4-cyanophenyl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

Produkt 1

HCID 68288974Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 25 mL round bottom flask containing a mixture of tert-butyl 4-(4-cyanophenyl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate and tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate (compound 40.2, 167 mg, 0.56 mmol) was added 10% palladium on carbon (40 mg) and ethyl acetate (6 mL). The system was purged with nitrogen then charged with hydrogen and stirred at room temperature. After purging the system with nitrogen, the mixture was filtered through celite and the filtrate was concentrated. The residue was purified by preparative TLC to obtain a colorless wax (77 mg, 45%). m/z (ES+) 245 (M minus t-butyl+H)+.

Aufarbeitung

  1. additionTo a 25 mL round bottom flask containing
  2. customThe system was purged with nitrogen
  3. additionthen charged with hydrogen
  4. customAfter purging the system with nitrogen
  5. filtrationthe mixture was filtered through celite
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by preparative TLC
  8. customto obtain a colorless wax (77 mg, 45%)

Quellen und Nachweise

ORD-Eintrag
ord-56a6a30c6025463cae99f8cfdfec9a05
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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