(1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester → tert-butyl (1R,3S,4S)-3-(aminomethyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 882795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882795
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH:15]CC2C=CC=CC=2)[C@@H:12]2[CH2:23][C@H:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH2:15])[C@@H:12]2[CH2:23][C@H:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 66865917(1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 66866957tert-butyl (1R,3S,4S)-3-(aminomethyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of (1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (39.8 mmol) in EtOH (120 mL) is treated with Pd/C (10%, 4.0 g) and stirred under a hydrogen atmosphere (7 bar) for 1 d. An additional amount of Pd/C (1.0 g) is added and the mixture is stirred for further 6 h under a hydrogen atmosphere (7 bar). After filtration through celite and removal of the solvents in vacuo the desired amine is obtained which is used without further purification. LC-MS (basic): tR=0.85 min; [M+H]+=227.3.

Aufarbeitung

  1. stirringthe mixture is stirred for further 6 h under a hydrogen atmosphere (7 bar)
  2. filtrationAfter filtration
  3. customthrough celite and removal of the solvents in vacuo the desired amine
  4. customis obtained which
  5. customis used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-11205cd6a04f4a65b28cc3f5567ee946
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236801B2

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