Ammonium Chloride → 1-(8-Benzyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine

HRID 2244501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244501
[N:1]1([C:6]2([C:16]#N)[CH2:15][CH2:14][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Mg]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[CH2:16]([C:6]1([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 3609768-(1-Pyrrolidinyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 178418336HCID 178418336, Verbindung

Produkt 1

HCID 685537551-(8-Benzyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 40.0 g 8-pyrrolidin-1-yl-1,4-dioxaspiro[4.5]decane-8-carbonitrile in 150 ml analytical grade tetrahydrofuran was added dropwise to 127 ml 2.0 molar benzylmagnesium chloride solution in THF under a nitrogen atmosphere and the mixture was stirred overnight at room temperature. For working up, 50 ml saturated ammonium chloride solution were added, while cooling with ice, the phases were separated, the aqueous phase was extracted three times with 50 ml diethyl ether each time, the combined organic phases were dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. The crude 1-(8-benzyl-1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidine obtained (54.0 g of yellow solid) was stirred, without further purification, with a mixture of 128 ml conc. hydrochloric acid (32 per cent by weight) and 74 ml water for 24 hours at room temperature. The reaction mixture was then first washed twice with 50 ml diethyl ether each time and then rendered alkaline by addition of sodium hydroxide solution (32 per cent by weight), while cooling with ice, and extracted three times with 100 ml methylene chloride each time, the combined methylene chloride extracts were dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. 40.3 g 4-benzyl-4-pyrrolidin-1-yl-cyclohexanone were obtained.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted three times with 50 ml diethyl ether each time
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-155df246bf8c4b368262385e37be57f1
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678834B2

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