Triphenylphosphine → 2-methyl-2-(4-nitro-1H-pyrazol-1-yl)propan-1-amine

HRID 714834Notes

Reaction equation

HRID 714834 reaction equation
[N:1]([CH2:4][C:5]([N:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[N:9]1)([CH3:7])[CH3:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[CH3:7][C:5]([N:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[N:9]1)([CH3:6])[CH2:4][NH2:1]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1178402371-(1-azido-2-methylpropan-2-yl)-4-nitro-1H-pyrazole

Product 1

HCID 825041082-methyl-2-(4-nitro-1H-pyrazol-1-yl)propan-1-amineYield 99.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 1-(1-azido-2-methylpropan-2-yl)-4-nitro-1H-pyrazole (10 g) obtained in Step C of Example 115 in a mixed solvent of tetrahydrofuran/water (v/v=10/1, 88 mL) was added triphenylphosphine (15 g), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (8.7 g) as a mixture with triphenylphosphine oxide.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-f42104d714724122bd1f495aca85cfbd
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

Loading…