Sodium borohydride → (7R,8R,9R)-10-Acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridine

HRID 2249709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2249709
[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C:7](=[O:19])[C@H:6]([OH:20])[C@H:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([OH:19])[C@H:6]([OH:20])[C@H:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 69290336(8R,9R)-10-acetyl-8-hydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Produkt 1

HCID 69288589(7R,8R,9R)-10-Acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

0.2 g (0.6 mmol) of (8R,9R)-10-acetyl-8-hydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one is dissolved in 15 ml of methanol and admixed with 40 mg (1.1 mmol) of sodium borohydride in portions with ice cooling. After 10 min, hydrolysis is effected using saturated sodium hydrogencarbonate solution and extraction using dichloromethane. The organic phase is dried over magnesium sulphate and evaporated. The residue is crystallized using diethyl ether. 0.16 g (80%) of the title compound is isolated as a colourless solid (m.p. 260-261° C.).

Aufarbeitung

  1. customhydrolysis
  2. extractionsodium hydrogencarbonate solution and extraction
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated
  5. customThe residue is crystallized

Quellen und Nachweise

ORD-Eintrag
ord-ea8179929f6e4adeb9b2132219a183d9
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314935B2

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