3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → Tert-butyl 3-(3-fluorophenyl)-3-hydroxyazetidine-1-carboxylate

HRID 72405Notes

Reaction equation

HRID 72405 reaction equation
[C:1]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:13][C:14]1[CH:15]=[C:16]([Mg]Br)[CH:17]=[CH:18][CH:19]=1>O1CCCC1.[NH4+].[Cl-]>[F:13][C:14]1[CH:19]=[C:18]([C:10]2([OH:12])[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178505773HCID 178505773, compound

Product 1

HCID 65918384Tert-butyl 3-(3-fluorophenyl)-3-hydroxyazetidine-1-carboxylateYield 105.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

1-Boc-3-azetidinone (500 mg, 2.77 mmol, available from Aldrich #696315) was dissolved in dry tetrahydrofuran (20 ml) under N2 atmosphere. The solution obtained was cooled at 0° C. and 3-Fluorophenylmagnesiumbromide (1M in THF) (3.33 ml, 3.33 mmol) was added dropwise under stirring. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was diluted with NH4Cl sat. sol. (50 ml) and the organics were extracted with ethylacetate (3×50 ml). Collected organics after solvent evaporation afforded the title compound (D28) (783 mg)

Workup

  1. customThe solution obtained
  2. temperatureThe reaction was warmed to room temperature
  3. stirringstirred overnight
  4. extractionthe organics were extracted with ethylacetate (3×50 ml)
  5. customCollected organics after solvent evaporation

Sources & evidence

ORD record
ord-25027c52db30406e9796a14ce3b04273
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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