Ammonium formate → 4-Amino-4-methyl-cyclohexanol

HRID 475381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475381
C(OC(=O)[NH:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)(C)C>[NH2:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 66756996benzyl N-(4-hydroxy-1-methylcyclohexyl)carbamate

Produkt 1

HCID 223798474-Amino-4-methyl-cyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of example 45E (169 mg, 0.64 mmol), ammonium formate (105 mg, 1.67 mmol) and 10% palladium on carbon (7 mg) in isopropanol (5 mL) was heated at 80° C. for 1 hour. The reaction mixture was cooled and filtered through a plug of Celite. The filter pad was washed with ethyl acetate (50 mL), and the filtrate was concentrated in vacuo to afford the titled compound as an inseparable mixture of diastereomers. MS (CI) m/z 130 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 3.77-3.71 (m, 2H), 3.65-3.61 (m, 2H), 1.87-1.61 (m, 4H), 1.63-1.33 (m, 10H), 1.15 (s, 3H), 1.11 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a plug of Celite
  3. washThe filter pad was washed with ethyl acetate (50 mL)
  4. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ca594bf58e5e4df3a43a692cb760ff13
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637546B2

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