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

HRID 1620671Notes

Reaction equation

HRID 1620671 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 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1R,2R)-2-aminocyclohexanol (1.00 g) in ethanol (30 mL) was added 4-thioxo-1,3-thiazolidin-2-one (1.17 g), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (971 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-862efa7b7aab4e0b95c279846eb8be90
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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