Sodium borohydride → (7R,8S,9R)-2,3,8-Trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 895595Notes

Reaction equation

HRID 895595 reaction equation
[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@:10]([CH3:21])([OH:20])[C:9](=[O:22])[C:8]=3[CH:7]=[CH:6][N:5]2[C:23]=1[CH3:24].[BH4-].[Na+]>CO>[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@:10]([CH3:21])([OH:20])[C@H:9]([OH:22])[C:8]=3[CH:7]=[CH:6][N:5]2[C:23]=1[CH3:24]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69551580(8S,9R)-2,3,8-Trimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 10308619(7R,8S,9R)-2,3,8-Trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridineYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8 g of (8S,9R)-2,3,8-trimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one are suspended in 160 ml of anhydrous methanol, and the suspension is treated with 2 g of sodium borohydride using a spatula and stirred at room temperature for 24 h, a solution being formed. It is then concentrated to dryness on a vacuum rotary evaporator, the residue is partitioned between water and dichloromethane (50 ml each), and the aqueous phase is adjusted to pH 8 using dilute hydrochloric acid and extracted twice with 200 ml of dichloromethane each time. The organic phases are combined, washed with a little water and dried over anhydrous sodium sulfate, the solvent is stripped off in vacuo and the residue obtained is washed with stirring in acetone. 5.3 g of the title compound are obtained as colorless crystals of melting point 180° C.

Workup

  1. customa solution being formed
  2. concentrationIt is then concentrated to dryness on a vacuum rotary evaporator
  3. customthe residue is partitioned between water and dichloromethane (50 ml each)
  4. extractionextracted twice with 200 ml of dichloromethane each time
  5. washwashed with a little water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe residue obtained
  8. washis washed
  9. stirringwith stirring in acetone

Sources & evidence

ORD record
ord-c338207052014fb09a1149f27727433c
Source dataset
uspto-grants-2005_07
Patent number
US06916825B2

Reaction notes

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