Sodium borohydride → HCID 10193644, compound

HRID 2121486Notes

Reaction equation

HRID 2121486 reaction equation
[BH4-].[Na+].[OH:3][C@H:4]1[C:13](=[O:14])[C:12]2[C:11]([CH2:15][O:16][CH3:17])=[CH:10][N:9]3[C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=[C:8]3[C:7]=2[NH:6][C@@H:5]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[OH:14][C@H:13]1[C:12]2[C:11]([CH2:15][O:16][CH3:17])=[CH:10][N:9]3[C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=[C:8]3[C:7]=2[NH:6][C@H:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@H:4]1[OH:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69997187HCID 69997187, compound

Product 1

HCID 10193644HCID 10193644, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, 0.2 g of sodium borohydride are added in small portions to 0.4 g of (8R, 9R)-8-hydroxy-6-methoxymethyl-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1 ,2-h][1,7]naphthyridin-7-one, dissolved in 20 ml of methanol, and the mixture is stirred at room temperature for 2 hours. The solvent is then removed under reduced pressure and the residue is admixed with water and extracted 3 times with methylene chloride. The organic phases are combined and concentrated to dryness in vacuo. Purification on silica gel (mobile phase: methylene chloride/methanol=100/3) gives 80 mg of the title compound [Rf=0.54 (methylene chloride/methanol=13/1)] of melting point 182-3° C. (decomp.).

Workup

  1. customThe solvent is then removed under reduced pressure
  2. extractionextracted 3 times with methylene chloride
  3. concentrationconcentrated to dryness in vacuo
  4. customPurification on silica gel (mobile phase: methylene chloride/methanol=100/3)

Sources & evidence

ORD record
ord-cbf384580a784ea88be747e6a0ff54cc
Source dataset
uspto-grants-2004_02
Patent number
US06696461B2

Reaction notes

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