Sodium hydride → HCID 22049033, compound

HRID 2087155Notes

Reaction equation

HRID 2087155 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-dc6ac5b88e5b45809949ec1ca207a4f3
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

Loading…