Ammonium formate → (S)-tert-butyl 4-aminoazepane-1-carboxylate

HRID 714535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714535
C1([C@H]([NH:9][C@H:10]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)C)C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[NH2:9][C@H:10]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 59027964tert-Butyl (S)-4-(((R)-1-phenylethyl)amino)azepane-1-carboxylate

Produkt 1

HCID 32639843(S)-tert-butyl 4-aminoazepane-1-carboxylateAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of Pd(OH)2/C (10%, 550 mg), tert-butyl (4S)-4-{[(1R)-1-phenylethyl]amino}azepane-1-carboxylate (5.5 g, 17.3 mmol) and HCOONH4 (3.3 g, 51.9 mmol) in MeOH (80 mL) was heated at reflux for 1.5 h. The reaction mixture was cooled to rt and filtered, the solvents of the filtrate were removed in vacuo. The residue was purified by column chromatography (gradient 0% to 10% MeOH in DCM) to give tert-butyl (4S)-4-aminoazepane-1-carboxylate (3.2 g, 87.3%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. filtrationfiltered
  4. customthe solvents of the filtrate were removed in vacuo
  5. customThe residue was purified by column chromatography (gradient 0% to 10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-b0f5a0c581f44aa792e754e23df3ccd2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187451B2

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