Water → 8-(2-Cyclopentyl-ethylidene)-1,4-dioxa-spiro[4.5]decane

HRID 2392763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2392763
Cl.[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12](C3C=CC=C(OC)C=3)([OH:15])[CH:11](CN(C)C)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:28][C:29]([O-:32])(C)C.[K+].O1C2(CCC(=O)CC2)OCC1.O>C1(C)C=CC=CC=1>[CH:2]1([CH2:7][CH:8]=[C:9]2[CH2:10][CH2:11][C:12]3([O:15][CH2:28][CH2:29][O:32]3)[CH2:13][CH2:14]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 23665647Potassium tert-butoxideHCID 67641018(1RS,2RS,4SR)-4-(cyclopentyl-ethyl)-2-dimethylaminomethyl-1-(3-methoxyphenyl)-cyclohexanol hydrochloride

Produkt 1

HCID 189804398-(2-Cyclopentyl-ethylidene)-1,4-dioxa-spiro[4.5]decaneAusbeute 245,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The reaction was conducted in a nitrogen atmosphere with the exclusion of moisture. 21.9 g (50 mmole) of compound (52) were added to 5.6 g (50 mmole) potassium tert-butylate in 400 ml toluene. The mixture was stirred for 30 minutes at room temperature and for 1 hour at 80° C., and was subsequently cooled to 60° C. 7.8 g (50 mmole) 1.4-dioxa-spiro[4.5]decan-8-one were added. The mixture was then stirred for 18 hours at 60° C. and cooled. 100 ml water were added drop-wise. The organic phase was separated off, the aqueous phase was extracted twice with toluene and dried over sodium sulphate, and the solvent was removed by distillation. 29 g oil were obtained, which was purified with 1:4 diisopropyl ether/n-hexane on a silica gel column.

Aufarbeitung

  1. temperaturewas subsequently cooled to 60° C
  2. stirringThe mixture was then stirred for 18 hours at 60° C.
  3. temperaturecooled
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted twice with toluene
  6. dry with materialdried over sodium sulphate
  7. customthe solvent was removed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-e35f16f36b5f4b249f7472c7f067843d
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05801201

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