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

HRID 444711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444711
[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-97c9a4d344754ef6bb32077e1b09944c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476224B2

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