Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate → Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylate

HRID 1986180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986180
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]#[N:17])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>O.C(O)C.N.[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][NH2:17])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 2

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 66660873Tert-butyl 4-(2-aminoethyl)-4-methylpiperidine-1-carboxylateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23948RhodiumKatalysatorHCID 222AmmoniaLösungsmittelHCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To 5% Rh/Al2O3 (0.600 g) suspended in water (2 mL) is added ethanol (5 mL), 4-cyanomethyl-4-methylpiperidine-1-carboxylic acid tert-butyl ester (0.258 g, 1.083 mmol) dissolved in ethanol (10 mL) and 28% NH3 (aq) (0.25 mL). The reaction mixture is subjected to 50 psi hydrogen gas and stirred at room temperature for 18 hours. The reaction mixture is filtered to remove the catalyst, then the filtrate is concentrated and chromatographed on silica gel, eluting with 0-10% (2 M NH3 in MeOH) in dichloromethane to give the title compound (130 mg, 50% yield).

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated
  4. customchromatographed on silica gel
  5. washeluting with 0-10% (2 M NH3 in MeOH) in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-6d8aea29b38a4ce88493911db2c68e8f
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547691B2

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