Phosphorus trichloride → 4-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1508995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508995
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N+:5]([O-])=[C:4]2[CH2:13][CH2:14][CH2:15][C:3]=12.P(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][C:3]=12

Komponenten

4

Edukt 2

HCID 24387Phosphorus trichlorideHCID 901107724-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine oxide

Produkt 1

HCID 901123734-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (0.079 g, 0.35 mmol) in methylene chloride (5 mL) was added phosphorous trichloride (0.096 g, 0.70 mmol). The mixture stirred at rt for 30 min. After this time, the mixture was quenched with a saturated solution of NaHCO3 and extracted with methylene chloride. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.057 g, 77%) as a clear oil. MW=211.69. 1H NMR (CDCl3, 300 MHz) δ 6.47 (s, 1H), 5.27-5.18 (m, 1H), 3.01-2.84 (m, 4H), 2.11 (quin, J=7.5 Hz, 2H), 1.31 (d, J=6.0 Hz, 6H); APCI MS m/z 212 [M+H]+.

Aufarbeitung

  1. customAfter this time, the mixture was quenched with a saturated solution of NaHCO3
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-79be5676ea8d42ba819c1d2d3af0385b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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