HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethylenediamine → HCID 67515261, compound

HRID 1400048
Notes
Print preview

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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906913B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes