Nitrogen → HCID 131734058, Verbindung

HRID 714216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714216
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][CH:9]1[F:21])C.CC(C[AlH]CC(C)C)C.[OH-].[Na+]>C1COCC1.C1(C)C=CC=CC=1.O>[F:21][C@H:9]1[C@@H:8]([CH2:7][CH2:6][OH:5])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 14487Diisobutylaluminum hydride2×HCID 14798Sodium HydroxideHCID 23512083HCID 23512083, Verbindung

Produkt 1

HCID 131734058HCID 131734058, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to an ice-cold solution of tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxylate (348 mg, 1.20 mmol) in dry THF (9 mL) was added DIBAL-H (2.41 mL of a 1M solution in toluene, 2.41 mmol). The reaction mixture was stirred at rt for 2 h. DIBAL-H (0.60 mL of a 1M solution in toluene, 0.60 mmol) was added again and the reaction mixture further stirred at rt for 1 h before being cooled to 0° C. Water (0.15 mL) was added followed by aq. 2N NaOH (0.30 mL). The mixture was stirred for 20 min, filtered through celite, washed with EA and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 7:3→1:1) to give the title compound as a colorless oil. LC-MS-conditions 08: tR=0.69 min; [M-CH3+H]+=233.35.

Aufarbeitung

  1. stirringthe reaction mixture further stirred at rt for 1 h
  2. temperaturebefore being cooled to 0° C
  3. stirringThe mixture was stirred for 20 min
  4. filtrationfiltered through celite
  5. washwashed with EA
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by FC (hept-EA, 7:3→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d46c42f8ac4046ecafccb067924b77c1
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187435B2

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