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

HRID 1530884Notes

Reaction equation

HRID 1530884 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][C:10]3[C:11](=[O:23])[C@H:12]([OH:22])[C@@H:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:14][C:15]=3[C:6]2=[N:5][C:4]=1[CH3:24])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:7]2[CH:8]=[CH:9][C:10]3[C@@H:11]([OH:23])[C@H:12]([OH:22])[C@@H:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:14][C:15]=3[C:6]2=[N:5][C:4]=1[CH3:24]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20640288(8r,9r)-3-Formyl-8-hydroxy-2-methyl-7-oxo-9-phenyl-7,8,9,10tetrahydroimidazo[1,2-h][1,7]naphthyridine

Product 1

HCID 9880354(7r,8r,9r)-3-Hydroxymethyl-7,8-dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridineYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.07 g of (8R,9R)-3-formyl-8-hydroxy-2-methyl-7-oxo-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine are dissolved in 5 ml of dry methanol, and 0.1 g of sodium borohydride is added. The mixture is stirred for 30 min and concentrated in vacuo. The oily residue is partitioned between water and chloroform. The organic layer is separated, dried over anhydrous sodium sulfate and concentrated. The product is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 9/1) to give 0.05 g of the title compound as a semi solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe oily residue is partitioned between water and chloroform
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe product is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-ca91940559c44edd8d96ee702df47ee2
Source dataset
uspto-grants-2001_03
Patent number
US06197783B1

Reaction notes

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