Water → HCID 69669257, compound

HRID 450564Notes

Reaction equation

HRID 450564 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:13][CH:12]([OH:14])[CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].F[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1.O>C1COCC1>[N+:22]([C:21]1[C:16]([O:14][CH:12]2[CH2:13][N:10]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:11]2)=[N:17][CH:18]=[CH:19][CH:20]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 27628172-Fluoro-3-nitropyridine

Product 1

HCID 69669257HCID 69669257, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% dispersion in oil, 2.30 g, 57.64 mmol) was added portionwise into a solution of 1-Boc-3-(hydroxy)azetidine (9.94 g, 57.64 mmol) in anhydrous THF (110 mL) at 0° C. and stirred for 0.5 hour. A solution of 2-fluoro-3-nitro-pyridine (7.80 g, 54.9 mmol) in anhydrous THF (15 mL) was added drop wise and the mixture allowed to warm to ambient temperature overnight. The mixture was cooled in an ice-bath and water (50 mL) added. The product was extracted with EtOAc, washed with water, brine and dried (Na2SO4). The product was purified by flash-column chromatography (petroleum ether (40-60° C.)/DCM) to yield the title compound as a yellow solid (4.37 g, 27%).

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. extractionThe product was extracted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customThe product was purified by flash-column chromatography (petroleum ether (40-60° C.)/DCM)

Sources & evidence

ORD record
ord-a989aa3963684f7bb1c3d816baad8df5
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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