Ethyl Acetate → HCID 59249261, compound

HRID 1807217Notes

Reaction equation

HRID 1807217 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][C@H:4]([OH:19])[CH2:5][O:6][C:7]([CH3:18])([CH3:17])[CH2:8][N:9]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[N:10]1.C(OCC)(=O)C.[H][H]>[Pd].C(O)C>[NH2:14][C:11]1[CH:12]=[CH:13][N:9]([CH2:8][C:7]([CH3:18])([CH3:17])[O:6][CH2:5][C@@H:4]([OH:19])[CH2:3][N:2]([CH3:1])[CH3:20])[N:10]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67296750HCID 67296750, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59249261HCID 59249261, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound (S)-1-dimethylamino-3-[1,1-dimethyl-2-(3-nitro-pyrazol-1-yl)-ethoxy]-propan-2-ol was prepared by reacting 1-[2-methyl-2-((S)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazole (0.39 g, 1.62 mmol), isopropyl alcohol (6 mL), and dimethylamine (3 mL, 6 mmol, 2 M in dioxane) under microwave conditions at 130° C. for 15 min. The mixture was extracted with dichloromethane and water. The organic layer was separated and the solvent evaporated under reduced pressure to yield (S)-1-dimethylamino-3-[1,1-dimethyl-2-(3-nitro-pyrazol-1-yl)-ethoxy]-propan-2-ol (0.4 g, 87%). This compound was reduced under the following conditions. The mixture of (S)-1-dimethylamino-3-[1,1-dimethyl-2-(3-nitro-pyrazol-1-yl)-ethoxy]-propan-2-ol (0.39 g, 1.66 mmol), ethyl acetate (30 mL), ethanol (30 mL) was added to a Parr bottle with 10% Pd/C (0.22 g) and subjected hydrogen gas (20 psi) for 2 h under the Parr Shaker Apparatus conditions. Work up by filtration via a glass membrane filter paper, solvent was removed under reduced pressure to afford (S)-1-[2-(3-amino-pyrazol-1-yl)-1,1-dimethyl-ethoxy]-3-dimethylamino-propan-2-ol as an oil (0.37 g, 97.5%).

Workup

  1. customfor 2 h
  2. filtrationWork up by filtration via a glass membrane
  3. filtrationfilter paper, solvent
  4. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-f966eae629c543a3940326d9f8fa46bf
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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