(1R,2R)-2-Aminocyclohexanol → HCID 178518169, compound

HRID 1620628Notes

Reaction equation

HRID 1620628 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].S=[C:10]1[CH2:14][S:13][C:12](=[O:15])[NH:11]1>C(O)C>[OH:8][C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]1[NH:1][C:10]1[CH2:14][S:13][C:12](=[O:15])[N:11]=1

Participants

4

Reactant 2

HCID 735777(1R,2R)-2-AminocyclohexanolHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-one

Product 1

HCID 178518169HCID 178518169, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trans-2-aminocyclohexanol (1.00 g) in ethanol (50 mL) was added 4-thioxo-1,3-thiazolidin-2-one (1.19 g), and the mixture was heated under reflux overnight. The reaction mixture was cooled to room temperature, the precipitate was removed, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, tetrahydrofuran). The obtained powder was washed with ethyl acetate to give the title compound (554 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customthe precipitate was removed
  4. customthe solvent of the filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, tetrahydrofuran)
  6. washThe obtained powder was washed with ethyl acetate

Sources & evidence

ORD record
ord-0a3bc08c5e03449e935c550194de1060
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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