Triethylamine → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

HRID 423640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423640
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([OH:9])[CH3:8])[CH2:3][CH2:2]1.[O:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O.CCN(CC)CC>ClCCCl>[OH:9][CH:7]([CH:4]1[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])[CH2:2][CH2:3]1)[CH3:8]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 3383211-(Piperidin-4-yl)ethan-1-ol

Produkt 1

HCID 21989903tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

(±)-1-(4-Piperidinyl)ethanol (see reference: WO 9725992A, 12.44 g, 65.7 mmol) in 1,2-dichloroethane (500 mL) was stirred at room temperature and BOC2O (14.36 g, 65.8 mmol) was added followed by Et3N (19 mL, 136 mmol). The stirred mixture was heated at gentle reflux for 15 min and then allowed to cool to room temperature and stirred overnight. The solution was washed twice with 10% citric acid, once with 10% Na2CO3, dried over MgSO4, filtered and concentrated to afford (±)-1,1-dimethylethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylate (14 g, 93% yield) as a light amber oil. 1H NMR (400 MHz, DMSO-d6): δ 4.35 (d, 1H, J=4.8 Hz), 3.92 (m, 2H), 3.32 (m, 1H), 2.59 (m, 2H), 1.68 (m, 1H), 1.47 (m, 1H), 1.34 (s, 9H), 1.25 (m, 1H), 1.08-0.88 (m, 2H), 0.97 (d, 3H, J=6.4 Hz).

Aufarbeitung

  1. temperatureThe stirred mixture was heated
  2. temperatureat gentle reflux for 15 min
  3. washThe solution was washed twice with 10% citric acid, once with 10% Na2CO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8e4caddd4a014e23a176eaaeb99c2806
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

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