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

HRID 895597Notes

Reaction equation

HRID 895597 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]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([OH:20])[C:9](=[O:28])[C:8]=3[CH:7]=[CH:6][N:5]2[C:29]=1[CH3:30].[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:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C@:10]([CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)([OH:20])[C@@H:9]([OH:28])[C:8]=3[CH:7]=[CH:6][N:5]2[C:29]=1[CH3:30]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20812187HCID 20812187, compound

Product 1

HCID 20812186(7S,8S,9R)-2,3-Dimethyl-8-benzyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]-naphthyridineYield 37.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.8 g of (8S,9R)-2,3-dimethyl-8-benzyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo-[1,2-h][1,7]naphthyridin-7-one suspended in 20 ml of methanol is treated in portions with 3.3 g of sodium borohydride (30 minutes), stirred at room temperature for 20 h and then refluxed for 5 h. It is then concentrated to dryness in vacuo and stirred into a mixture of 20 ml of water and 20 ml of dichloromethane, the mixture is adjusted to pH 8 using dilute hydrochloric acid with cooling, after separating off the aqueous phase this is extracted a further three times with 50 ml of dichloromethane each time, and the organic phases are combined, washed with a little water and concentrated to dryness in vacuo on a rotary evaporator. The residue obtained is purified on silica gel (eluent: dichloromethane/methanol 13/1). 0.3 g of the title compound of melting point 115-22° C. (diisopropyl ether) are obtained.

Workup

  1. temperaturerefluxed for 5 h
  2. concentrationIt is then concentrated to dryness in vacuo
  3. stirringstirred into a mixture of 20 ml of water and 20 ml of dichloromethane
  4. temperaturewith cooling
  5. customafter separating off the aqueous phase
  6. extractionthis is extracted a further three times with 50 ml of dichloromethane each time
  7. washwashed with a little water
  8. concentrationconcentrated to dryness in vacuo on a rotary evaporator
  9. customThe residue obtained
  10. customis purified on silica gel (eluent: dichloromethane/methanol 13/1)

Sources & evidence

ORD record
ord-6c0a9f32e9fa451c96370a4fa991e73c
Source dataset
uspto-grants-2005_07
Patent number
US06916825B2

Reaction notes

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