Tert-butyl 3-benzoylpiperidine-1-carboxylate → Tert-butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate

HRID 1254188

Reaktionsgleichung

Reaktionsgleichung von HRID 1254188
[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Mg]Br)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1COCC1>[OH:8][C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

4

Edukt 2

HCID 57449677Tert-butyl 3-benzoylpiperidine-1-carboxylateHCID 178444609HCID 178444609, Verbindung

Produkt 1

HCID 59382974Tert-butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a 100-mL round bottom flask were added tert-butyl 3-(benzoyl)piperidine-1-carboxylate (0.4733 g, 1.63 mmol, 1.0 equiv) and THF (5 mL). The flask was evacuated and refilled with N2. The mixture was cooled with a dry ice-acetone bath and hexylmagnesium bromide (2.0M solution in Et2O, 2.5 mL, 5.0 mmol, 3.0 equiv) was added. The reaction mixture was allowed to slowly warm to −10° C. while stirring overnight (17 h). The mixture was quenched with saturated NH4Cl (10 mL), extracted three times with EtOAc, and dried over Na2SO4. The crude product was purified by reversed-phase HPLC(XTerra® Prep MS C18 OBD™ Column, 5 μl, 19×50 mm, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min, flow rate 20 mL/min) to give tert-butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate. LC-MS (3 min) tR=2.41 min, m/z 398 (M+Na+), 376 (MH+), 302, 276, 258.

Aufarbeitung

  1. customThe flask was evacuated
  2. additionrefilled with N2
  3. temperatureThe mixture was cooled with a dry ice-acetone bath
  4. customThe mixture was quenched with saturated NH4Cl (10 mL)
  5. extractionextracted three times with EtOAc
  6. dry with materialdried over Na2SO4
  7. customThe crude product was purified by reversed-phase HPLC(XTerra® Prep MS C18 OBD™ Column, 5 μl, 19×50 mm, 10%
  8. customover 8 min

Quellen und Nachweise

ORD-Eintrag
ord-f77450e355d84c85840777653ca5231b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455521B2

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