Diethyl Ether → HCID 76071550, compound

HRID 927033Notes

Reaction equation

HRID 927033 reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)(C)(C)C.Cl.O1CCOCC1.C(OCC)C>O1CCOCC1>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13]([C:9]3[C:8]([NH2:7])=[CH:12][O:11][N:10]=3)=[CH:18][CH:17]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 204431481,4-Dioxane hydrochlorideHCID 90204243HCID 90204243, compound

Product 1

HCID 76071550HCID 76071550, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

{3-[4-(4-Fluoro-benzyloxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester (1.97 g, 5.13 mmol) was dissolved in 30 mL of dioxane and 30 mL of 4 N HCl/dioxane was added. The reaction was stirred at rt for 4 h and allowed to stand overnight. The resulting crystalline mass was mixed with diethyl ether (20 mL) and stirred for 10 min. The suspension was filtered off and washed with a total of 20 mL of diethyl ether. The filter cake was partitioned between ethyl acetate and 5% NaHCO3 solution and the organic phase separated. The aqueous phase was extracted with once more with ethyl acetate. The combined organic phases were washed twice with brine and dried over Na2SO4. Filtration followed by removal of volatiles under reduced pressure gave 3-[4-(4-fluoro-benzyloxy)-phenyl]-isoxazol-4-ylamine (1.32 g, 91%) as an off-white solid. M+1=285.2

Workup

  1. waitto stand overnight
  2. stirringstirred for 10 min
  3. filtrationThe suspension was filtered off
  4. washwashed with a total of 20 mL of diethyl ether
  5. customThe filter cake was partitioned between ethyl acetate and 5% NaHCO3 solution
  6. customthe organic phase separated
  7. extractionThe aqueous phase was extracted with once more with ethyl acetate
  8. washThe combined organic phases were washed twice with brine
  9. dry with materialdried over Na2SO4
  10. filtrationFiltration
  11. customfollowed by removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-1a0786dfe06f48deb5cd71b4bd1849a9
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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