(R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone → (R)-tert-butyl 2-methylpiperidin-3-ylcarbamate
Reaktionsgleichung
C(OC([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16](=O)[CH3:17])=O)C1C=CC=CC=1>CC(O)C.[Pd]>[CH3:17][C@@H:16]1[CH:15]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:14][CH2:13][CH2:12][NH:11]1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
(R)-6-(Benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone (306) (14.3 g, 39.3 mmol) was divided in 2 equal batches and each batch was dissolved in IPA (70 mL), combined with 10% Pd/C (5.5 g), and hydrogenated on a Parr shaker at 50 psi pressure for 12 hours. The batches were combined, filtered through celite and concentrated in vacuo to give (R)-tert-butyl 2-methylpiperidin-3-ylcarbamate (307), (8.2 g, 38 mmol, 97% yield) as a clear oil.