Tert-butyl 3-(trichloromethyl)oxaziridine-2-carboxylate → Tert-butyl 2-(3-benzylpentan-3-yl)hydrazinecarboxylate

HRID 244958Notes

Reaction equation

HRID 244958 reaction equation
[CH2:1]([C:8]([NH2:13])([CH2:11][CH3:12])[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C1O[N:17]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>C(Cl)Cl>[CH2:1]([C:8]([NH:13][NH:17][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH2:11][CH3:12])[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11139943Tert-butyl 3-(trichloromethyl)oxaziridine-2-carboxylateHCID 185063513-Benzylpentan-3-amine

Product 1

HCID 89807785Tert-butyl 2-(3-benzylpentan-3-yl)hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.68 g of 3-benzylpentan-3-amine was dissolved in 20 mL of methylene chloride, mixed with 4.8 g (18 mmol) of separately prepared t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate under cooling with ice and stirred at room temperature for 30 mitues, and the reaction solution was washed with 10% aquoeous 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 30 g, ethyl acetate:hexane=0:100 to 20:80) to give 1.62 g of the desired product as a light brown solid.

Workup

  1. temperatureunder cooling with ice
  2. washthe reaction solution was washed with 10% aquoeous 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 30 g, ethyl acetate:hexane=0:100 to 20:80)

Sources & evidence

ORD record
ord-8626551945ce448d8df94b3086dac069
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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