Tetrahydrofuran → HCID 58367545, compound

HRID 729479Notes

Reaction equation

HRID 729479 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[K+].C1COCC1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1F>CN(C=O)C>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[O:12][CH:10]1[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 676741-Bromo-2,4-difluorobenzeneHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 58367545HCID 58367545, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Boc-3-hydroxyazetidine (1.50 g, 8.67 mmol) in DMF (9.1 mL) was added 1 M potassium tert-butoxide in THF (9.96 mL, 9.96 mmol) followed by 1-bromo-2,4-difluorobenzene (2.50 g, 13.0 mmol). After a period of 1 h at 50° C., the reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (15% ethyl acetate in hexane) to provide the title compound as a white solid.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-54014c727c5346cba488ed09ec19cfb8
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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