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Methanol → 2-(Diphenylmethyl)-5-oxa-2,8-diazaspiro[3.5]nonane

HRID 471040
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 471040
CSC.B.[CH:5]([N:18]1[CH2:21][C:20]2([CH2:26][NH:25][C:24](=O)[CH2:23][O:22]2)[CH2:19]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CO.CNCCNC>C1COCC1>[CH:5]([N:18]1[CH2:21][C:20]2([CH2:26][NH:25][CH2:24][CH2:23][O:22]2)[CH2:19]1)([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8070N,N'-DimethylethylenediamineHCID 12423031(Dimethyl sulfide)trihydroboronHCID 579892642-Benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-7-one

Produkt 1

HCID 579892372-(Diphenylmethyl)-5-oxa-2,8-diazaspiro[3.5]nonane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Borane methyl sulfide complex (2M in THF, 10.7 mL) was added to a solution of 2-benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-7-one (example 33, step e) (2 g) in dry THF (40 mL) and the resultant solution was stirred at 70° C. under nitrogen for 50 minutes. The mixture was cooled to room temperature and treated dropwise with methanol (40 mL) followed by N1,N2-dimethylethane-1,2-diamine (3.43 g). The mixture was heated at 70° C. for 6 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 1% triethylamine and 5% methanol in dichloromethane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.35 g.

Aufarbeitung

  1. temperatureThe mixture was heated at 70° C. for 6 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and brine
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-26fb8fad8c7d459396052a25a85a995e
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629271B2

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