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

HRID 2304479
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Reaktionsgleichung

Reaktionsgleichung von HRID 2304479
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10]([OH:20])[C:9](=[O:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23].[BH4-].[Na+]>CO.O>[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10]([OH:20])[C@H:9]([OH:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23]
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5

Edukt 2

HCID 4311764Sodium borohydrideHCID 59943673(8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Produkt 1

HCID 10215014(7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962
Water
Lösungsmittel

Versuchsvorschrift

6 g (19.52 mmol) of (8R,9R)-2,3-dimethyl 8 hydroxy-9-phenyl-7,8,9,10-tetra-hydroimidazo-[1,2-h][1,7]naphthyridin-7-one (see >90% Dalcet Chiralcel HPLC) are suspended in 60 ml of methanol and cooled to −5° to 0° C. in a methanol-ice bath. At this temperature, sodium borohydride (0.81 g, 21.47 mmol) is added by spatula during the course of 0.5 h (evolution of gas). After addition is complete, the mixture is stirred for a further 10 min, and then concentrated in a vacuum rotary evaporator at a bath temperature of 40° C. The oily residue obtained is taken up in distilled water and extracted three times with chloroform. The organic phases are combined and washed with a little water, then dried using anhydrous sodium sulfate and filtered. The filtrate is concentrated on a vacuum rotary evaporator and co-evaporated with acetone; the title compound crystallizes out in the course of this. The precipitate is filtered off, washed with acetone and dried to constant weight at 50° C. in a vacuum drying oven. 5.15 g (85.3%, ee>90%, Daicel Chiralcel HPLC) of the title compound are obtained as a colorless crystallize of melting point 206-9° C.

Aufarbeitung

  1. temperaturecooled to −5° to 0° C. in a methanol-ice bath
  2. additionAfter addition
  3. concentrationconcentrated in a vacuum rotary evaporator at a bath temperature of 40° C
  4. customThe oily residue obtained
  5. extractionextracted three times with chloroform
  6. washwashed with a little water
  7. customdried
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated on a vacuum rotary evaporator and co-evaporated with acetone
  10. customthe title compound crystallizes out in the course of this
  11. filtrationThe precipitate is filtered off
  12. washwashed with acetone
  13. customdried to constant weight at 50° C. in a vacuum
  14. customdrying oven

Quellen und Nachweise

ORD-Eintrag
ord-1381876530c84dc79c356d8da76d30e5
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06436953B1

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