(+-)-3-Quinuclidinol → Quinuclidin-3-yl2-bromophenylcarbamate

HRID 2281257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2281257
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[H-].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]=[C:20]=[O:21]>C1COCC1>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20](=[O:21])[O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

Komponenten

5

Edukt 3

HCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 1370972-Bromophenyl isocyanate

Produkt 1

HCID 68327765Quinuclidin-3-yl2-bromophenylcarbamateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of quinuclidin-3-ol (382 mg, 3.00 mmol) in THF (15 mL) was added NaH [60% dispersion in mineral oil](156 mg, 3.90 mmol) at room temperature. The mixture was stirred for 15 min and 2-bromophenyl isocyanate (594 mg, 3.00 mmol) was added under stirring. The resulting mixture was stirred at room temperature for 18 h, quenched with brine and extracted with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting crude product was purified by silica gel column chromatography (EtOAc/methanol 3:1) to give the product quinuclidin-3-yl 2-bromophenylcarbamate as viscous oil (0.80 g, 82%).

Aufarbeitung

  1. stirringunder stirring
  2. stirringThe resulting mixture was stirred at room temperature for 18 h
  3. customquenched with brine
  4. extractionextracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatography (EtOAc/methanol 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-a04cc68ceed8444e8bff8a2f3ea6feee
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139580B2

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