N-BOC-ethylenediamine → tert-butyl N-(2-((cyclopropylmethyl)amino)ethyl)carbamate

HRID 220834Notes

Reaction equation

HRID 220834 reaction equation
C(=O)([O-])O.[K+].BrC[CH2:8][CH:9]1[CH2:11][CH2:10]1.[C:12]([O:16][C:17](=[O:22])[NH:18][CH2:19][CH2:20][NH2:21])([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[C:12]([O:16][C:17](=[O:22])[NH:18][CH2:19][CH2:20][NH:21][CH2:10][CH:11]1[CH2:8][CH2:9]1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 516893Potassium BicarbonateHCID 22636989(2-Bromoethyl)cyclopropane

Product 1

HCID 45092182tert-butyl N-(2-((cyclopropylmethyl)amino)ethyl)carbamateYield 30.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
66 °C

Procedure

Potassium hydrogen carbonate (220 mg, 2.2 mmol) and (bromoethyl)cyclopropane (270 mg, 2.0 mmol) were added to a solution of tert-butyl-N-(2-aminoethyl)carbamate (320 mg, 2.0 mmol) in THF (10 ml). The mixture was heated at 66° C. for 20 h and solvents were concentrated in vacuo. The residue was dissolved in chloroform, washed with water, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% triethylamine:4% methanol:95% chloroform) to yield the title compound (130 mg, 30%).

Workup

  1. concentrationsolvents were concentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; 1% triethylamine:4% methanol:95% chloroform)

Sources & evidence

ORD record
ord-e7733171b3cf4154b41ba834829b5ca5
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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