Hydrochloric Acid → 4-Butyl-4-(pyrrolidin-1-yl)cyclohexanone

HRID 2422394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422394
O.Cl.[CH2:3]([C:7]1([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6].[OH-].[Na+]>CC(C)=O>[CH2:3]([C:7]1([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 574751141-(8-Butyl-1,4-dioxaspiro[4,5]dec-8-yl)pyrrolidine

Produkt 1

HCID 574751134-Butyl-4-(pyrrolidin-1-yl)cyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Water (10.0 ml) and 37% hydrochloric acid (14.0 ml) were added to a solution of 1-(8-butyl-1,4-dioxaspiro[4,5]dec-8-yl)pyrrolidine (2.70 g, 10.1 mmol) in acetone (100 ml) and the mixture was stirred overnight at room temperature. Then 4 M sodium hydroxide solution was added slowly to the mixture until a pH of 10 was achieved. The mixture was extracted with diethyl ether (4×40 ml), the combined organic phases were dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (2.6 g) was purified by flash chromatography (260 g, 30×5.6 cm) with ethyl acetate/methanol (9:1). Yield: 1.06 g (47%), brown oil.

Aufarbeitung

  1. extractionThe mixture was extracted with diethyl ether (4×40 ml)
  2. dry with materialthe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated to small volume under vacuum
  4. customThe crude product (2.6 g) was purified by flash chromatography (260 g, 30×5.6 cm) with ethyl acetate/methanol (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5fe226b265bc4a29a7b4722b3a2a1b04
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960404B2

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