Water → Fadrozole

HRID 478010

Reaktionsgleichung

Reaktionsgleichung von HRID 478010
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)#[N:3].C(O)[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO.O>CO>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1)#[N:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 59694Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)-, hydrochloride (1:1)HCID 444041beta-Cyclodextrin

Produkt 1

HCID 59693Fadrozole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Racemic 5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride is applied, in 20 mg aliquots, to a 4.6×250 mm beta-cyclodextrin bonded silica gel column using 7:3 water:methanol as the eluant at a flow rate of 0.8 ml/min. The separate fractions are evaporated under vacuum to yield (-)-5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, [α]D25 =-89.2° and (+)-5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, [α]D25 +85.02°. Both compounds are separately dissolved in acetone and treated with 1 molar equivalent of etheral hydrogen chloride to yield the hydrochloride salts, m.p. 82°-83° (amorphous) and m.p. 218°-220°, respectively.

Aufarbeitung

  1. customThe separate fractions are evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3427e2b968df4d80b42364faa1f02820
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889861

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