Potassium Carbonate → (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 584847Notes

Reaction equation

HRID 584847 reaction equation
C([C@@H:4]1[C:13](=[O:14])[C:12]2[CH:11]=[CH:10][N:9]3[C:15]([CH3:19])=[C:16]([CH3:18])[N:17]=[C:8]3[C:7]=2[N:6]([C:20](=[O:22])[CH3:21])[C@H:5]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)C.[BH4-].[Na+].C(=O)([O-])[O-:32].[K+].[K+]>CO>[C:20]([N:6]1[C:7]2[C:8]3=[N:17][C:16]([CH3:18])=[C:15]([CH3:19])[N:9]3[CH:10]=[CH:11][C:12]=2[C@@H:13]([OH:14])[C@H:4]([OH:32])[C@H:5]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 69551346(8R,9R)-8,10-Diacetyl-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 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]naphthyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

64 g of (8R,9R)-8,10-diacetyl-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one (crude product) are dissolved in 250 ml of methanol. 12.3 g of sodium borohydride are introduced with ice cooling. After stirring for 1 h, 23 g of potassium carbonate are added to the reaction mixture and it is stirred for a further 2 h at room temperature. It is then added to ice water and the precipitate is filtered off with suction. After washing the precipitate with acetone and ether, 37 g of the title compound are isolated.

Workup

  1. stirringis stirred for a further 2 h at room temperature
  2. filtrationthe precipitate is filtered off with suction
  3. washAfter washing the precipitate with acetone and ether, 37 g of the title compound
  4. customare isolated

Sources & evidence

ORD record
ord-0d85e2b28f944666a19eaf4d2deb0f01
Source dataset
uspto-grants-2005_08
Patent number
US06927292B2

Reaction notes

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