1-Benzylcyclopropylamine → Tert-butyl 2-(1-benzylcyclopropyl)hydrazinecarboxylate

HRID 244957Notes

Reaction equation

HRID 244957 reaction equation
[CH2:1]([C:8]1([NH2:11])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C1O[N:15]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(Cl)Cl>[CH2:1]([C:8]1([NH:11][NH:15][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1529231-BenzylcyclopropylamineHCID 11139943Tert-butyl 3-(trichloromethyl)oxaziridine-2-carboxylate

Product 1

HCID 89808294Tert-butyl 2-(1-benzylcyclopropyl)hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.6 g (72.0 mmol) of 1-benzylcyclopropanamine was dissolved in 90 mL of methylene chloride, mixed with 14.3 g (54.5 mmol) of separately prepared t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate under cooling with ice, and stirred at room temperature for 30 minutes. After completion of the reaction, methylene chloride was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (silica gel 350 g, ethyl acetate:hexane=1:20) to give 4.6 g of the desired product as a brown solid.

Workup

  1. temperatureunder cooling with ice
  2. distillationwas distilled off under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (silica gel 350 g, ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-5a244dd0248041a5beb4f00ced7e4bce
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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