(S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-yl(methyl)carbamate → (S)-1'-(5-ethylpyrimidin-2-yl)-3-(methylamino)-1,4'-bipiperidin-2-one

HRID 407974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407974
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([N:21](C)[C:22](=O)OCC4C=CC=CC=4)[C:16]3=[O:33])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([NH:21][CH3:22])[C:16]3=[O:33])[CH2:13][CH2:14]2)=[N:7][CH:8]=1)[CH3:2]

Komponenten

4

Edukt 1

HCID 86688111(S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-yl(methyl)carbamate

Produkt 1

HCID 67470730(S)-1'-(5-ethylpyrimidin-2-yl)-3-(methylamino)-1,4'-bipiperidin-2-oneAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

(S)-benzyl 1′-(5-ethylpyrimidin-2-yl)-2-oxo-1,4′-bipiperidin-3-yl(methyl)carbamate (0.100 g, 0.22 mmol) was dissolved in methanol (5 mL). 10% Pd/C (10 mg) was added and the reaction mixture was stirred under hydrogen balloon pressure overnight. The reaction was filtered and concentrated and purified over silica gel (100% EtOAc) to afford (S)-1′-(5-ethylpyrimidin-2-yl)-3-(methylamino)-1,4′-bipiperidin-2-one (40 mg, 0.13 mmol, 57% yield).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified over silica gel (100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-378bacfadc464c2fb804a4b6bdc387ba
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754226B2

Notizen zur Reaktion

Wird geladen…