Tetrahydrofuran → HCID 117849124, compound

HRID 1477587Notes

Reaction equation

HRID 1477587 reaction equation
O1CCCC1.[OH:6][CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1.[H-].[Na+].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>C(OCC)(=O)C.O>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][O:6][CH:7]2[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10]2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 117849124HCID 117849124, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (2.0 mL) of tert-butyl 3-hydroxyazetidine-1-carboxylate (87 mg, 0.50 mmol), sodium hydride (33 mg, 0.75 mmol, purity 55%) was added at 0° C. and the resultant solution was stirred for 30 minutes. Subsequently, 4-fluorobenzyl bromide (62.3 μL, 0.50 mmol) was added to the reaction solution and the resultant mixture was stirred at room temperature for 19 hours. After completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant mixture was performed three times. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (68.5 mg, yield 49%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1a62f771c35346cb96d41f904f94339a
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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