Benzyl Bromide → (+/-)-cis-N1-Benzyl-N 2-tert-butoxycarbonyl-1,2-cyclohexanediamine

HRID 459474Notes

Reaction equation

HRID 459474 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[CH2:23]([NH:15][C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 1514392(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine

Product 1

HCID 58822072(+/-)-cis-N1-Benzyl-N 2-tert-butoxycarbonyl-1,2-cyclohexanediamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(±)-cis-N-tert-Butoxycarbonyl-1,2-cyclohexanediamine (3.78 g) was dissolved in acetonitrile (80 ml), and to the solution triethylamine (2.44 ml) and benzyl bromide (2.10 ml) were added, and the mixture was stirred at room temperature for 13 hours. The solvent was distilled off under reduced pressure, dichloromethane and water was added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (3.08 g) as a pale orange oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, dichloromethane and water
  2. additionwas added to the residue
  3. customto separate an organic layer
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4f7c2bf4c8ee46b0b4372c62153c9f47
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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