Water → 1-Benzyl-3-phenyl-piperidin-3-ol

HRID 324544

Reaktionsgleichung

[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1COCC1.O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 1-benzyl-3-piperidinone (0.193 g, 1.02 mmol) in toluene dry (10 mL) cooled at 0° C. was added a solution of phenyl magnesium bromide 3.1M in THF (0.48 mL, 1.4 mmol). The resulting solution was maintained at 0° C. for 2 h, then was allowed to warm at 25° C. for 1 h. Water (50 mL) was added and the mixture was extracted with EtOAc (2×50 mL). The collected organic phase was dried and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel using EtOAc/cyclohexane as eluant to afford the title compound as a white solid (0.235 g, 80%). 1H NMR (CDCl3): 1.65-1.85 (m, 3H), 1.9-2.15 (m, 1H), 2.067 (bd, J=8.1 Hz, 1H), 2.34 (d, J=11.1 Hz, 1H), 2.77 (d, J=11.1 Hz, 1H), 2.95 (bd, J=8.1 Hz, 1H), 3.60 (s, 2H), 4.005 (bs, 1H), 7.2-7.4 (m, 8H), 7.50 (s, 1H), 7.525 (s, 1H).

Aufarbeitung

temperatureThe resulting solution was maintained at 0° C. for 2 h
temperatureto warm at 25° C. for 1 h
extractionthe mixture was extracted with EtOAc (2×50 mL)
customThe collected organic phase was dried
concentrationconcentrated under reduced pressure
customThe crude compound was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-85f8712dce0a4789a3775707b50bbda7
Quelldatensatz: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06218404B1

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