1-Benzyl-4-piperidone → 1,4-Dibenzylpiperidin-4-ol
Reaktionsgleichung
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([N:17]1[CH2:22][CH2:21][C:20]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([OH:23])[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of benzyl magnesium chloride (40 ml of 2.0 M soln. in THF, 80 mmol)in THF (80 ml) was added 1-benzyl-4-piperidinone (7.4 ml, 40 mmol) over 7 min. and stirred overnight. The o reaction mixture was poured over ice and extracted with ether (2×). The combined ether extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo to a pale green syrup. This material was chromatographed on silica with 50-60% EtOAc/hexane as eluent. The appropriate fractions were combined and concentrated in vacuo to afford the product as an off white solid.