Phosphorus oxychloride → Tert-butyl 4-(4-cyanophenyl)-3,6-dihydropyridine-1(2h)-carboxylate

HRID 541180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541180
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 59003435Tert-butyl 4-(4-cyanophenyl)-4-hydroxypiperidine-1-carboxylate2×

Produkt 1

HCID 11289112Tert-butyl 4-(4-cyanophenyl)-3,6-dihydropyridine-1(2h)-carboxylateAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Into a round-bottom flask, was placed a solution of tert-butyl 4-(4-cyanophenyl)-4-hydroxypiperidine-1-carboxylate (compound 1.2, 2 g, 6.61 mmol, 1.00 equiv) in pyridine (40 mL). POCl3 (10.16 g, 66.26 mmol, 10.02 equiv) was carefully added. The resulting mixture was stirred under nitrogen overnight at room temperature and then concentrated under vacuum. The residue was taken up in 20 mL of DCM, washed with 2×20 mL of sodium bicarbonate (aq), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with PE/EtOAc (100:1-30:1) as eluent to yield 1.4 g (74%) of the title compound as a white solid.

Aufarbeitung

  1. customInto a round-bottom flask, was placed
  2. concentrationconcentrated under vacuum
  3. washwashed with 2×20 mL of sodium bicarbonate (aq)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-1577c826758d43b5879d3577b9cf0bc6
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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