HCID 67315659, compound → HCID 86641305, compound

HRID 2059921Notes

Reaction equation

HRID 2059921 reaction equation
[C:1]([C:3]1([N:21]2[CH2:24][C:23]([F:26])([F:25])[CH2:22]2)[CH2:20][CH2:19][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4]1)#N.[C:27]1([Mg]Br)[CH:32]=[CH:31]C=[CH:29][CH:28]=1>C1COCC1>[F:25][C:23]1([F:26])[CH2:24][N:21]([C:3]2([C:1]3[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=3)[CH2:4][CH2:5][C:6]3([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:8][CH2:7]3)[CH2:19][CH2:20]2)[CH2:22]1

Participants

4

Reactant 2

HCID 67315659HCID 67315659, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 86641305HCID 86641305, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude tert-butyl 9-cyano-9-(3,3-difluoroazetidin-1-yl)-3-azaspiro[5.5]-undecane-3-carboxylate was taken up in THF (20 ml) and PhMgBr (12 ml) was added at 0° C. The reaction mixture was stirred at room temperature overnight. The mixture was quenched with NH4Cl solution at 0° C. and was then extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by column chromatography (silica gel (100-200)) to obtain the desired compound. Yield: 31%

Workup

  1. customThe mixture was quenched with NH4Cl solution at 0° C.
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel (100-200))

Sources & evidence

ORD record
ord-1f2b1dbd63944416948d21869f17492d
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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