4-(Benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester → 4-(Tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester

HRID 2361582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361582
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([N:14](CC2C=CC=CC=2)[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CCO.[Pd]>[C:1]([O:5][C:6]([CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 687254864-(Benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 687250694-(Tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl esterAusbeute 104,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester (300 mg, 0.7433 mmol) in EtOH (10 mL) is added 10% Pd/C (wet) (40 mg). The mixture stirs under a blanket of hydrogen gas at atmospheric pressure for 12 h. The mixture is then filtered though celite. The celite is washed with MeOH (50 mL). The filtrated is concentrated to afford 243 mg of 4-(tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-D6) δ ppm 0.98 (m, 2H), 1.25 (m, 2H), 1.36 (m, 9H), 1.41 (m, 9H), 1.81 (m, 4H), 2.05 (m, 1H), 2.28 (m, 1H), 3.20 (m, 2H).

Aufarbeitung

  1. filtrationThe mixture is then filtered though celite
  2. washThe celite is washed with MeOH (50 mL)
  3. concentrationThe filtrated is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e763996afe8c4eec8f61fc5b01874551
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691756B2

Notizen zur Reaktion

Wird geladen…