Acetone → HCID 23156168, compound

HRID 1890625Notes

Reaction equation

HRID 1890625 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:28]=[CH:27][C:18]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:20])=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[BH4-].[Na+].CC(C)=O>C(O)C>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:28]=[CH:27][C:18]([CH:19]([OH:20])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 11326145HCID 11326145, compound

Product 1

HCID 23156168HCID 23156168, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1 (2.27 g, 6.14 mmol) was dissolved in ethanol (50 mL), and sodium borohydride (0.465 g, 12.3 mmol) was added to the solution, followed by stirring at room temperature for 2 hours. The reaction mixture was added with acetone and stirred for 30 minutes, then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=40:1), and obtained crystals were triturated with diethyl ether-hexane to obtain Compound 2 (2.10 g, yield 92%).

Workup

  1. stirringstirred for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=40:1)
  8. customobtained crystals
  9. customwere triturated with diethyl ether-hexane

Sources & evidence

ORD record
ord-fc69386a2f124fd896ffd4249fc7dba4
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

Loading…