Water → (S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine

HRID 2192893Notes

Reaction equation

HRID 2192893 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH2:6])=[N:2]1.[OH-].[K+].Cl[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]1.O>CS(C)=O>[CH3:16][C:13]1([CH3:17])[O:12][C@@H:11]([CH2:10][N:1]2[CH:5]=[CH:4][C:3]([NH2:6])=[N:2]2)[CH2:15][O:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 178418806HCID 178418806, compound

Product 1

HCID 57346939(S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 1H-pyrazol-3-amine in DMSO (15 mL) was added potassium hydroxide (3.18 g) at room temperature. After stirring at room temperature for 30 minutes, to the reaction mixture was added a solution of (R)-(+)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane (3.0 g) in DMSO (10 mL), followed by stirring at room temperature for 3 days. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained crude product was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1-1:3) to obtain 1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrazol-3-amine (1.0 g) as a pale violet oily substance.

Workup

  1. stirringby stirring at room temperature for 3 days
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained crude product
  6. customwas purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1-1:3)

Sources & evidence

ORD record
ord-011b8153b1bf4763ba1279f71a8d7deb
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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