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Ammonium Chloride → tert-Butyl 1-methyl-1-hydroxyspiro[indane-3,4'-piperidine]-1'-carboxylate

HRID 1027135
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1027135
[O:1]=[C:2]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH2:3]1.[CH3:23][Mg]Cl.C1COCC1.[Cl-].[NH4+]>C1COCC1>[CH3:23][C:2]1([OH:1])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH2:3]1
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Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 18673579Tert-butyl 3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateHCID 178420676HCID 178420676, Verbindung

Produkt 1

HCID 67082928tert-Butyl 1-methyl-1-hydroxyspiro[indane-3,4'-piperidine]-1'-carboxylateAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

tert-Butyl 1-oxospiro[indane-3,4′-piperidine]-1′-carboxylate (0.202 g, 0.671 mmol) was dissolved in THF (3 mL), 3 mmol/L methylmagnesium chloride-THF solution (0.450 mL, 1.34 mmol) was added under ice-cooling, and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture, and the mixture was extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give the title compound (0.141 g, 66%).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted several times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-f2a3572f76904e478cfe487f894fec4b
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729264B2

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