Nitrogen → tert-Butyl 3,3-difluoro-4-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 714209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714209
N#N.C([O:5][C:6](=O)[CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]1([F:22])[F:21])C.CC(C[AlH]CC(C)C)C.[OH-].[Na+]>C1COCC1.O>[F:22][C:9]1([F:21])[CH:8]([CH2:7][CH2:6][OH:5])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:10]1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 73977801Tert-butyl 4-(2-ethoxy-2-oxoethyl)-3,3-difluoropiperidine-1-carboxylate

Produkt 1

HCID 86695049tert-Butyl 3,3-difluoro-4-(2-hydroxyethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of tert-butyl 4-(2-ethoxy-2-oxoethyl)-3,3-difluoropiperidine-1-carboxylate (177 mg, 0.57 mmol) in dry THF (5.8 mL) was added DIBAL-H (1.0 M solution in THF, 1.15 mL, 1.15 mmol) at 0° C. The reaction mixture was stirred at rt for 2 h. The mixture was cooled down to 0° C., successively treated with H2O (0.23 mL) and 2N aq. NaOH (0.45 mL). The mixture was stirred at rt for 20 min, filtered through celite, washed with EA and the filtrate concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 1:1→1:2) and the title compound obtained as a colorless oil. LC-MS-conditions 08: tR=0.74 min; [M-CH3+H]+=251.34.

Aufarbeitung

  1. temperatureThe mixture was cooled down to 0° C.
  2. stirringThe mixture was stirred at rt for 20 min
  3. filtrationfiltered through celite
  4. washwashed with EA
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe crude residue was purified by FC (hept-EA, 1:1→1:2)

Quellen und Nachweise

ORD-Eintrag
ord-71299ff893e843beab2d0e6722a11f9a
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187435B2

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