1,2-Butanediol → HCID 66799967, compound

HRID 1528288Notes

Reaction equation

HRID 1528288 reaction equation
[C@@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:7].[CH2:9](O)[CH:10](O)[CH2:11][CH3:12]>C[C-]1C(C)=C(C)C(C)=C1C.C[C-]1C(C)=C(C)C(C)=C1C.[Cl-].[Cl-].[Cl-].[Cl-].[Ir+3].[Ir+3].C(=O)(O)[O-].[Na+]>[CH2:10]([C@@H:11]1[CH2:12][NH:8][C@@H:1]2[C@H:2]([CH2:3][CH2:4][CH2:5][CH2:6]2)[NH:7]1)[CH3:9]

Participants

5

Reactant 2

HCID 114291,2-ButanediolHCID 438061,2-Diaminocyclohexane, trans-

Product 1

HCID 66799967HCID 66799967, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 7603074312354-84-6Catalyst

Procedure

Dichloro(pentamethylcyclopentadienyl)iridium (III) dimer (70 mg, 0.090 mmol) and sodium bicarbonate (73 mg, 0.87 mmol) were added to an aqueous (20 mL) solution of trans-cyclohexane-1,2-diamine (2.00 g, 17.5 mmol) and (±)-1,2-butanediol (1.69 mL, 18.4 mmol) with stirring at room temperature. Degassing and argon substitution were repeated 3 times, and the mixture was then stirred for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (methylene chloride/methanol) to obtain (2R*,4aS*,8aS*)-2-ethyldecahydroquinoxaline (2.03 g, yield: 69%) in a yellow solid form.

Workup

  1. customDegassing
  2. stirringthe mixture was then stirred for 24 hours
  3. temperatureunder reflux
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (methylene chloride/methanol)

Sources & evidence

ORD record
ord-f162d1b9aed64ee9bdad18bd456c7028
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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