2-Methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amine → Tert-butyl 2-(2-methyl-1-(4-(trifluoromethyl)phenyl)propan-2-yl)hydrazinecarboxylate

HRID 244955Notes

Reaction equation

HRID 244955 reaction equation
[CH3:1][C:2]([NH2:15])([CH3:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1.ClC(Cl)(Cl)C1O[N:19]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C(Cl)Cl>[CH3:14][C:2]([NH:15][NH:19][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH3:1])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 1209942-Methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amineHCID 11139943Tert-butyl 3-(trichloromethyl)oxaziridine-2-carboxylate

Product 1

HCID 89808109Tert-butyl 2-(2-methyl-1-(4-(trifluoromethyl)phenyl)propan-2-yl)hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.2 g of 2-methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amine was dissolved in 30 mL of methylene chloride and mixed with 5.6 g (21 mmol) of separately prepared t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate under cooling with ice. The reaction solution was stirred at room temperature for 30 minutes, washed with 10% aqueous citric acid, with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively and dried over anhydrous sodium sulfate, and methylene chloride was removed under reduced pressure. The resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel 100 g, ethyl acetate:hexane) to give 1.38 g of the desired product as a white solid.

Workup

  1. temperatureunder cooling with ice
  2. washwashed with 10% aqueous citric acid, with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively
  3. dry with materialdried over anhydrous sodium sulfate, and methylene chloride
  4. customwas removed under reduced pressure
  5. customThe resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel 100 g, ethyl acetate:hexane)

Sources & evidence

ORD record
ord-d6588baa6c404aae9f5dc2266a68097b
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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