Ammonia → 3-[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]-1,3-oxazolidin-2-one

HRID 2056775Notes

Reaction equation

HRID 2056775 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.[O:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20].[C@@H]1(N)CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].N>O1CCOCC1.[Cu]I>[OH:13][CH2:12][CH2:11][C@H:10]1[C:5]2[CH:4]=[CH:3][C:2]([N:17]3[CH2:18][CH2:19][O:15][C:16]3=[O:20])=[CH:14][C:6]=2[CH2:7][CH2:8][O:9]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 739492-OxazolidinoneHCID 536878432-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol

Product 1

HCID 693072903-[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (0.815 g, 3.17 mmol) in dry dioxan (5 mL) was added 1,3-oxazolidin-2-one (0.26 g, 2.95 mmol), trans-1,2-cyclohexanediamine (0.05 mL, 0.42 mmol), copper(I) iodide (0.040 g, 0.21 mmol) and potassium carbonate (1.02 g, 7.36 mmol), and the mixture heated at reflux under nitrogen overnight. 2M Ammonia was added and the mixture extracted into dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica to yield the title compound.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux under nitrogen overnight
  3. extractionthe mixture extracted into dichloromethane
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-2ecd0758c762451f8f10f76f4782c687
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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