Ethylenediamine → HCID 67515261, compound

HRID 1400048Notes

Reaction equation

HRID 1400048 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH:18]2[C:16]([C:20]3[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=3)([CH2:17]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[NH:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].C(N)CN>C1(C)C=CC=CC=1.[Cu]I>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH:18]2[C:16]([C:20]3[CH:25]=[CH:24][C:23]([N:27]4[CH2:31][CH2:30][CH2:29][C:28]4=[O:32])=[CH:22][CH:21]=3)([CH2:17]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 53432548tert-Butyl 1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate2×

Product 1

HCID 67515261HCID 67515261, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent2×

Procedure

To a stifling suspension of potassium carbonate (1.23 g, 8.95 mmol) and CuI (42.5 mg, 0.22 mmol) in anhydrous toluene (10 mL) were added 1-(4-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (Intermediate I, 1.6 g, 4.5 mmol) dissolved in toluene (10 mL) followed by addition of pyrrolidinone (0.5 mL, 6.2 mmol) and ethylene diamine (0.03 mL, 0.45 mmol). Reaction mixture was refluxed for 16 h. Reaction mixture was then concentrated and the crude product was purified by column chromatography (silica gel, 4:6 EtOAc:Pet. ether) to afford the title compound as white solid (800 mg, 52%).

Workup

  1. customReaction mixture
  2. temperaturewas refluxed for 16 h
  3. customReaction mixture
  4. concentrationwas then concentrated
  5. customthe crude product was purified by column chromatography (silica gel, 4:6 EtOAc:Pet. ether)

Sources & evidence

ORD record
ord-e1d9b1d09d0e453fa733bf497cba1917
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

Loading…