Cesium carbonate → (S)-1-(5-methyl-4-nitro-1H-pyrazol-1-yl)propan-2-ol

HRID 522690

Reaction equation

HRID 522690 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[N+:7]([O-:9])=[O:8].[CH3:10][C@H:11]1[CH2:13][O:12]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][C:2]1[N:6]([CH2:10][C@@H:11]([OH:12])[CH3:13])[N:5]=[CH:4][C:3]=1[N+:7]([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 792551H-Pyrazole, 3-methyl-4-nitro-HCID 146262(2S)-2-Methyloxirane

Product 1

HCID 118023522(S)-1-(5-methyl-4-nitro-1H-pyrazol-1-yl)propan-2-olYield 9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 5-methyl-4-nitro-1H-pyrazole (2.5 g, 19.7 mmol) in acetonitrile (100 mL) was added (S)-2-methyloxirane (1.37 g, 23.6 mmol) and cesium carbonate (19.3 g, 59.1 mmol). The mixture was stirred at 30° C. for 7 days, then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by Prep-HPLC and then chiral-HPLC to give (S)-1-(5-methyl-4-nitro-1H-pyrazol-1-yl)propan-2-ol (0.33 g) as a yellowish solid. MS (ES+) C7H11N3O3 requires: 185, found: 186 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-baaa67abe8c24741b659995bc628d4d5
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Linked notes

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