Sodium hydride → HCID 22049033, compound

HRID 1832162Notes

Reaction equation

HRID 1832162 reaction equation
C([O:5][C:6](=[O:20])[NH:7][CH:8]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1)[CH2:9]O)(C)(C)C.[H-].[Na+]>C1COCC1>[F:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[F:18])[CH2:11][CH:8]1[CH2:9][O:20][C:6](=[O:5])[NH:7]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

A solution of (+)-[1-(3,4-difluorobenzyl)-2-hydroxy-ethyl]-carbamic acid-tert-butyl ester (1.00 g, 4.00 mmol) in THF (10 mL) was added via a dropping funnel to a stirring suspension of 95% NaH (0.12 g, 5.0 mmol) in THF (20 mL) at room temperature. The resulting suspension was stirred for 3 h and then quenched carefully with water (10 mL). The biphasic mixture was extracted with Et2O (50 mL), washed with brine, filtered and the solvent was removed, in vacuo. The resulting gummy residue was purified by column chromatography (Rf=0.25, 3:2 hexane-EtOAc), to give the desired product as a white solid (0.320 g, 76%).

Workup

  1. customquenched carefully with water (10 mL)
  2. extractionThe biphasic mixture was extracted with Et2O (50 mL)
  3. washwashed with brine
  4. filtrationfiltered
  5. customthe solvent was removed, in vacuo
  6. customThe resulting gummy residue was purified by column chromatography (Rf=0.25, 3:2 hexane-EtOAc)

Sources & evidence

ORD record
ord-43c2f9a8359e411a8f2f20c56e748190
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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