Phenyl isocyanate → N-phenylquinuclidin-3-yloxycarboxamide

HRID 609640

Reaktionsgleichung

Reaktionsgleichung von HRID 609640
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:17](=[O:18])[NH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:2]2

Komponenten

3

Edukt 2

HCID 7672Phenyl isocyanateHCID 15381(+-)-3-Quinuclidinol

Produkt 1

HCID 3945131N-phenylquinuclidin-3-yloxycarboxamideAusbeute 86 %

Versuchsvorschrift

1-Azabicyclo[2.2.2]octan-3-ol and phenyl isocyanate were used. The residual solid resulting from the above described procedure was purified via column chromatography eluting with a 1:10 ratio of methanol:chloroform to afford the title compound (86%) as a white solid: NMR (CDCl3)δ7.60-7.0 (m, 5H, Ph), 4.81 (m, 1H, CH-OCO), 3.27 (m, 1H, one of NCH2C-O), 2.9 (m, 5H, N(CH2)2 and one of NCH2C-O), 2.1 (m, 1H, methine at C4), 2.05-1.30 (m, 4H, CH2 at C5 and C8); FAB LRMS m /z (relative intensity, %) 247 ([MH+ ], 100).

Aufarbeitung

  1. customThe residual solid resulting from the above described procedure
  2. customwas purified via column chromatography
  3. washeluting with a 1:10 ratio of methanol

Quellen und Nachweise

ORD-Eintrag
ord-f1a288bbe7c14ff3b6cd02c4f98b0b17
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998429

Verknüpfte Notizen

Wird geladen…