1,5-Dibromopentane → HCID 178453979, compound

HRID 1920128Notes

Reaction equation

HRID 1920128 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>C(O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([N:15]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 178419079HCID 178419079, compound

Product 1

HCID 178453979HCID 178453979, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Trans-4-tert-butoxycarbonylamino-aminocyclohexane (1 g) and potassium carbonate (1.3 g) were suspended in ethanol (20 mL), and then 1,5-dibromopentane (1.07 g) was added thereto. The reaction solution was stirred at 80° C. for 48 hours. After the reaction solution was cooled to room temperature, the solvent was concentrated under reduced pressure. The residue was dissolved in water (50 mL). The aqueous layer was extracted twice with dichloromethane (50 mL). The combined organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. After removing the anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (ethyl acetate: 10%-saturated aqueous ammonia-methanol=1:0→10:1) to obtain the title compound (492 mg) having the following physical properties.

Workup

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. concentrationthe solvent was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (50 mL)
  4. extractionThe aqueous layer was extracted twice with dichloromethane (50 mL)
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing the anhydrous sodium sulfate
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated
  10. customThe residue was purified by silica gel chromatography (ethyl acetate: 10%-saturated aqueous ammonia-methanol=1:0→10:1)

Sources & evidence

ORD record
ord-6e9b8862df2945e48b7be9b0604850c7
Source dataset
uspto-grants-2012_05
Patent number
US08168783B2

Reaction notes

Loading…