Triethylamine → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2424842Notes

Reaction equation

HRID 2424842 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:16]=[CH:15][C:8]2[O:9][C:10]([CH3:14])([CH3:13])[O:11][CH2:12][C:7]=2[CH:6]=1)[OH:4].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:14][C:10]1([CH3:13])[O:9][C:8]2[CH:15]=[CH:16][C:5]([C@H:3]3[O:4][C:17](=[O:18])[NH:1][CH2:2]3)=[CH:6][C:7]=2[CH2:12][O:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

Product 1

HCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 57.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (2.53 g, 11.3 mmol) in chloroform (12 mL) was added carbonyldiimidazol (2.75 g, 17 mmol) and triethylamine (2.37 mL, 17 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue diluted with ethyl acetate (25 mL). The organic layer was washed with water (2×10 mL), brine (10 mL), dried (Na2SO4), and the solvent reduced under reduced pressure. Purification by column chromatography with silica gel and n-hexane/ethyl acetate (1:2) as eluent yielded the title compound (1.63 g, 51%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with ethyl acetate (25 mL)
  3. washThe organic layer was washed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customPurification by column chromatography with silica gel and n-hexane/ethyl acetate (1:2) as eluent

Sources & evidence

ORD record
ord-44c6c5af5c9043828c266be9328f6734
Source dataset
uspto-grants-2011_06
Patent number
US07964615B2

Reaction notes

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