Benzyl Bromide → HCID 21913792, compound

HRID 911243Notes

Reaction equation

HRID 911243 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:10][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 21913792HCID 21913792, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

Dissolve tert-butyl-N-(2-hydroxyethyl)-carbamate (10 mL, 64.5 mmol) in anhydrous THY (500 mL) at 0° C. Add sodium hydride (60% in mineral oil, 3.1 g, 77.4 mmol) and stir for 30 min at 0° C. Add benzyl bromide (9.2 mL, 77 mmol) followed by tetrabutylammonium iodide (3.7 g, 10 mmol) and stir at ambient temperature overnight. Quench with water (500 mL), extract with diethyl ether (3×100 mL), wash the combined organic extracts with brine, dry over MgSO4, filter, and evaporate to give the desired intermediate (5 g), that was used without further purification.

Workup

  1. customQuench with water (500 mL)
  2. extractionextract with diethyl ether (3×100 mL)
  3. washwash the combined organic extracts with brine
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. customevaporate

Sources & evidence

ORD record
ord-9e12870181044dd48373619ebd9811bb
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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