4-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester → tert-Butyl 4-aminocyclohexane-1-carboxylate

HRID 2361579

Reaktionsgleichung

Reaktionsgleichung von HRID 2361579
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([NH:14]C(OCC2C=CC=CC=2)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([CH:8]1[CH2:9][CH2:10][CH:11]([NH2:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 538881934-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 18698345tert-Butyl 4-aminocyclohexane-1-carboxylateAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester (3.0 g, 9.009 mmol) in THF (80 mL) is added TEA (0.24 mL, 1.724 mmol) and 10% Pd/C (wet) (420 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 1.8 g of 4-amino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 200, Rt=0.39 min (method 6).

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-2d00f2d377a64ca7be09e92204c8a186
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691756B2

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