Sodium hydride → HCID 22049033, compound

HRID 1275221Notes

Reaction equation

HRID 1275221 reaction equation
[H-].[Na+].C([O:7][C:8](=[O:22])[NH:9][CH:10]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)[CH2:11]O)(C)(C)C>C1COCC1>[F:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[F:20])[CH2:13][CH:10]1[CH2:11][O:22][C:8](=[O:7])[NH:9]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 22048830Carbamic acid, [2-(3,4-difluorophenyl)-1-(hydroxymethyl)ethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 22049033HCID 22049033, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a well stirred suspension of 95% NaH (0.12 g, 5.0 mmol) in THF (20 mL) at r.t. was added a solution of (+)-[1-(3,4-difluorobenzyl)-2-hydroxy-ethyl]-carbamic acid-tert-butyl ester (1.0 g; 4.0 mmol) in 10 mL THF via a dropping funnel at room temperature. The resulting suspension was stirred for 3 h and then quenched carefully with 10 mL of water. The biphasic mixture was extracted with 50 mL of Et2O, washed with brine, filtered and the solvent was removed in vacuo. The gummy residue thus obtained was purified by column chromatography over silica gel (Rf =0.25, 3:2 hexane-EtOAc) to obtain (+)-4-(3,4-difluoro-benzyl)-oxazolidin-2-one as a white solid (0.32 g, 76%).

Workup

  1. stirringThe resulting suspension was stirred for 3 h
  2. customquenched carefully with 10 mL of water
  3. extractionThe biphasic mixture was extracted with 50 mL of Et2O
  4. washwashed with brine
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe gummy residue thus obtained
  8. customwas purified by column chromatography over silica gel (Rf =0.25, 3:2 hexane-EtOAc)

Sources & evidence

ORD record
ord-4027649398e34d1498696a41a942f428
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

Loading…