Benzyl 4-formylpiperidine-1-carboxylate → HCID 68313085, Verbindung
Reaktionsgleichung
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH3:20]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([OH:18])[CH2:19][CH3:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 4-formylpiperidine-1-carboxylic acid benzyl ester (1.0 g, 4.04 mmol) in THF (15 mL) at 0° C. was added ethylmagnesium bromide (1.0M in THF, 8.1 mL, 8.08 mmol) and the mixture was stirred at 0° for 1 h. The reaction mixture was then quenched with water and extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-100% EtOAc in hexane) affording 4-(1-Hydroxypropyl)piperidine-1-carboxylic acid benzyl ester (690 mg, 62%). 1H NMR (CDCl3, 400 MHz): δ 7.38-7.27 (5H, m), 5.13 (2H, bs), 4.25 (2H, s), 3.36-3.29 (1H, m), 2.83-2.66 (2H, m), 1.85-1.77 (1H, bd, J=13.16 Hz), 1.64-1.19 (7H, m), 0.97 (3H, t, J=7.41 Hz).