2-Methyl-1-(4-methylphenyl)propan-2-amine → Tert-butyl 2-(2-methyl-1-(p-tolyl)propan-2-yl)hydrazinecarboxylate

HRID 244931Notes

Reaction equation

HRID 244931 reaction equation
[CH3:1][C:2]([NH2:12])([CH3:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.ClC(Cl)(Cl)C1O[N:16]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C(Cl)Cl>[CH3:11][C:2]([NH:12][NH:16][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 1164872-Methyl-1-(4-methylphenyl)propan-2-amineHCID 11139943Tert-butyl 3-(trichloromethyl)oxaziridine-2-carboxylate

Product 1

HCID 86697472Tert-butyl 2-(2-methyl-1-(p-tolyl)propan-2-yl)hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.40 g (14.7 mmol) of separately prepared 2-methyl-1-p-tolylpropan-2-amine was dissolved in 20 mL of methylene chloride, and 2.60 g (10.0 mmol) of separately prepared t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate in 10 mL of methylene chloride was added under cooling with ice. The reaction slution was stirred under cooling with ice for 30 minutes and at room temperature for 1 hour, and the methylene chloride was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (100:0 to 0:100) as the eluent to give 1.61 g of the desired product as colorless crystals.

Workup

  1. temperatureunder cooling with ice
  2. customthe methylene chloride was removed under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ab7833a35ac74b8baff2f9726d12b506
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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