Ethyl Acetate → 1-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-1H-pyrazol-3-ylamine

HRID 1807097Notes

Reaction equation

HRID 1807097 reaction equation
[CH3:1][C:2]([O:13][CH2:14][C@H:15]1[CH2:17][O:16]1)([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[N:5]1.C(OCC)(=O)C.[H][H]>C(O)C>[CH3:12][C:2]([O:13][CH2:14][C@H:15]1[CH2:17][O:16]1)([CH3:1])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([NH2:9])=[N:5]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 592496401-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 592494671-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-1H-pyrazol-3-ylamineYield 103.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazole (0.3 g, 1.24 mmol), and ethyl acetate (15 mL), ethanol (15 mL) was subjected to the H-Cube (Thales Nano) at 1 mL/min at 10° C., 10 psi hydrogen. The first time through not completely reduced. Resubjected and complete reduction of nitro group by NMR. Solvent was removed under reduced pressure to afford 1-[2-methyl-2-((R)-1-oxiranylmethoxy)-propyl]-1H-pyrazol-3ylamine as an oil (0.27 g, 100%).

Workup

  1. customwas subjected to the H-Cube (Thales Nano) at 1 mL/min at 10° C.
  2. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9eb85ad0131646a0806f6873551df409
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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