(+-)-3-Quinuclidinol → HCID 23295075, Verbindung

HRID 1955260

Reaktionsgleichung

Reaktionsgleichung von HRID 1955260
[C:1]1([C:7]2([C:10]([Cl:12])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]([OH:21])[CH2:14]2>>[ClH:12].[C:1]1([C:7]2([C:10]([O:21][CH:15]3[CH:16]4[CH2:19][CH2:20][N:13]([CH2:18][CH2:17]4)[CH2:14]3)=[O:11])[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 2

HCID 15381(+-)-3-QuinuclidinolHCID 27603721-Phenyl-cyclopropanecarbonyl chloride

Produkt 1

HCID 23295075HCID 23295075, Verbindung

Versuchsvorschrift

The title compound was prepared in analogous manner to that in Example 4. The 1-phenylcyclopropanecarbonyl chloride obtained after the chlorination step was reacted with 3-quinuclidinol at 80° C. for 21 h. The reaction mixture was filtered and chromatographed on silica gel using toluene-Et3N 95:5 as eluent. The yield was 0.76 g (40%); mp 229-233° C.; 1H NMR (D2O) δ 1.42-1.48 (m, 2H), 1.72-1.78 (m, 2H), 1.81-1.98 (m, 3H), 2.10 (m, 1H), 2.40 (m, 1H), 3.14 (m, 1H), 3.25-3.41 (m, 4H), 3.71 (m, 1H), 5.17 (m, 1H), 7.44 (m, 1H), 7.49 (m, 2H), 7.55 (m, 2H) Anal. (C17H21NO2.HCl) C, H, N.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5be22b69c7474dbe8a403dd64579881e
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124354

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