Sodium hydride → HCID 67388892, compound

HRID 908442Notes

Reaction equation

HRID 908442 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1.Br[CH2:16][CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.O>[CH2:19]([O:18][CH2:17][CH2:16][O:3][CH:4]1[CH2:5][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 67388892HCID 67388892, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (2.03 g, 60% in oil) was added portionwise to a ice-cooled solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (8 g) in DMF (20 ml). The mixture was stirred at 0° C. for 20 minutes and benzyl 2-bromoethyl ether (8.03 ml) was added. The mixture was heated at 80° C. for 18 hours. After cooling, the mixture was diluted in water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Evaporation of the solvent and chromatography on silica gel (eluting with 20% to 50% ethyl acetate in petroleum ether gave tert-butyl 3-(2-benzyloxyethoxy)azetidine-1-carboxylate (9.15 g).

Workup

  1. temperatureThe mixture was heated at 80° C. for 18 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent and chromatography on silica gel (
  7. washeluting with 20% to 50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0a8be6b243af49d8ae79b5fc72e5d7c3
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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