Pyrindan → 6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide

HRID 1499437

Reaktionsgleichung

Reaktionsgleichung von HRID 1499437
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]2[CH2:18][CH2:19][CH2:20][C:13]=12>C(Cl)Cl>[N+:12]1([O-:9])[CH:17]=[CH:16][CH:15]=[C:14]2[CH2:18][CH2:19][CH2:20][C:13]=12

Komponenten

4

Edukt 2

HCID 68292PyrindanHCID 70297m-Chloroperbenzoic acid

Produkt 1

HCID 131533156,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxideAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

mCPBA (10.0 g, 44.6 mmol) was added slowly to a mixture of 6,7-dihydro-5H-cyclopenta[b]pyridine (from Aldrich, 5.0 g, 42 mmol) in DCM (50 mL). The reaction mixture was stirred at room temperature for 2 h. The solution was then washed with aq. Na2S2O3 (50 mL) and 1 M NaOH (50 mL). The aqueous layer was extracted with DCM (5×70 mL). The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound (4.5 g, 79%). LCMS calc. for C8H10NO (M+H)+: m/z=136.1. Found: 136.2.

Aufarbeitung

  1. washThe solution was then washed with aq. Na2S2O3 (50 mL) and 1 M NaOH (50 mL)
  2. extractionThe aqueous layer was extracted with DCM (5×70 mL)
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-00cd6614197d4f68ba06c2f88a5c8a77
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

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