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Potassium Bromide → 2-(4-Isopropoxy-phenyl)-2-aza-spiro[4.5]decane-1,8-dione

HRID 2368806
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2368806
[OH:1][CH:2]1[CH2:22][CH2:21][C:5]2([C:9](=[O:10])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].C(=O)(O)[O-].[Na+]>ClCCl.O.Cl[O-].[Na+]>[CH:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:21][CH2:22][C:2](=[O:1])[CH2:3][CH2:4]3)[C:9]2=[O:10])=[CH:12][CH:13]=1)([CH3:20])[CH3:19]
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Komponenten

8

Edukt 4

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 58230130HCID 58230130, Verbindung

Produkt 1

HCID 582300492-(4-Isopropoxy-phenyl)-2-aza-spiro[4.5]decane-1,8-dioneAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 23665760Sodium HypochloriteLösungsmittel

Versuchsvorschrift

To a solution of 8-hydroxy-2-(4-isopropoxy-phenyl)-2-aza-spiro[4.5]decan-1-one (7 g) and 2,2,6,6-tetramethylpiperidine-1-oxyl (721 mg) in dichloromethane (250 ml) were added sequentially a solution of potassium bromide (549 mg) in water (60 ml), sodium hypochlorite (52.8 ml), sodium bicarbonate (5.81 g) and the reaction mixture was then stirred for 3 hour at RT. The reaction mixture was poured into ice/water and extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated off. The residue was purified by flash chromatography (silica gel, gradient 0% to 50% ethyl acetate in heptane) to give the title compound as a brown solid (5 g). MS (m/e): 302.174 [MH+].

Aufarbeitung

  1. extractionextracted three times with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated off
  6. customThe residue was purified by flash chromatography (silica gel, gradient 0% to 50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-6cfad00cd7be4ff892de14b08e4542eb
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08703807B2

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