1,2-Diaminocyclohexane, trans- → HCID 68578315, compound

HRID 886959Notes

Reaction equation

HRID 886959 reaction equation
Br[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[O:20]1[CH2:24][C:23](=O)[N:22]=[C-:21]1.P([O-])([O-])([O-])=[O:27].[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>C(OCC)(=O)C.O.O1CCOCC1.CN(C)C=O>[O:27]=[C:21]1[N:22]([C:2]2[C:12]3[O:11][CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:23][CH2:24][O:20]1

Participants

9

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 532495662H-1,3-oxazol-2-id-4-oneHCID 59403519Tert-butyl 9-bromo-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylate

Product 1

HCID 68578315HCID 68578315, compoundYield 68.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-Butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (328 mg, 1.00 mmol), 2-oxazolidone (87.0 mg, 1.00 mmol), tripotassium phosphate (318 mg, 1.50 mmol), N,N-dimethylformamide (3 ml), dioxane (3 ml) and 1,2-trans-cyclohexanediamine (0.025 ml) was stirred at room temperature under a nitrogen atmosphere for 5 min. Copper iodide(I) (35.0 mg, 0.184 mmol) was added, and the mixture was stirred at 110° C. under a nitrogen atmosphere for 20 hr. The reaction mixture was poured into water (10 ml) and ethyl acetate (10 ml), and filtered through celite. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (230 mg, 68.9%) as an oil.

Workup

  1. stirringthe mixture was stirred at 110° C. under a nitrogen atmosphere for 20 hr
  2. filtrationfiltered through celite
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ee0f4366d9244a41a1f76e2d33de4f53
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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