Water → (7R,8R,9R)-7,8-Dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 985085Notes

Reaction equation

HRID 985085 reaction equation
[OH:1][C@H:2]1[C:11](=[O:12])[C:10]2[CH:9]=[CH:8][N:7]3[CH:13]=[C:14]([CH3:16])[N:15]=[C:6]3[C:5]=2[NH:4][C@@H:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+].O>CC(O)C.C[O-].[Na+]>[OH:12][C@@H:11]1[C:10]2[CH:9]=[CH:8][N:7]3[CH:13]=[C:14]([CH3:16])[N:15]=[C:6]3[C:5]=2[NH:4][C@H:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:2]1[OH:1]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 69586463(8R,9R)-8-Hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 10125504(7R,8R,9R)-7,8-Dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 10942334Sodium MethoxideSolvent2×

Procedure

6 g (20.5 mmol) of (8R,9R)-8-hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one are suspended in 30 ml of 2-propanol and 2 ml of 0.3% strength methanolic sodium methoxide solution. 0.4 g (10.2 mmol) of sodium borohydride, dissolved in 5 ml of 0.3% methanolic sodium methoxide solution, is added dropwise at 10° C. in the course of 10 minutes. The reaction mixture (suspension) is stirred overnight at room temperature (a solution forms in the course of this). The reaction solution is added to 90 ml of water and extracted three times with 30 ml of ethyl acetate each time. The combined ethyl acetate phases are washed once with water and concentrated. The residue is chromatographed on silica gel (ethyl acetate/2-propanol 95:5). The product fractions are concentrated and crystallized using diethyl ether. The crystals are filtered off with suction and dried at 50° C. in a high vacuum. 4.3 g (71% of theory) of the title compound of m.p. 119° C. (decomposition) are obtained.

Workup

  1. additionis added dropwise at 10° C. in the course of 10 minutes
  2. extractionextracted three times with 30 ml of ethyl acetate each time
  3. washThe combined ethyl acetate phases are washed once with water
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (ethyl acetate/2-propanol 95:5)
  6. concentrationThe product fractions are concentrated
  7. customcrystallized
  8. filtrationThe crystals are filtered off with suction
  9. customdried at 50° C. in a high vacuum

Sources & evidence

ORD record
ord-5d76011074964191ae14af7571b2956d
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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