Ammonium Chloride → HCID 22248599, compound

HRID 890127Notes

Reaction equation

HRID 890127 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:19][CH2:18][CH:17]2[CH:13]([CH2:14][CH2:15][C:16]2=[O:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][C:69]=1[F:74].CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:19][CH2:18][CH:17]2[CH:13]([CH2:14][CH:15]([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][C:69]=3[F:74])[C:16]2=[O:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 612591-Bromo-2-fluorobenzeneHCID 634876Binap, (A+-)-HCID 22248215HCID 22248215, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 22248599HCID 22248599, compoundYield 51.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

After adding 191 mg of 3-benzyloxycarbonyl-7-oxo-3-azabicyclo[4.3.0]nonane, 16 mg of palladium acetate and 104 mg of BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) to 3 ml of toluene under a nitrogen atmosphere, the mixture was stirred for 15 minutes, and then 245 mg of o-bromofluorobenzene, 134 mg of sodium tert-butoxide and 6 ml of toluene were added and the mixture was stirred overnight at 100° C. Saturated aqueous ammonium chloride solution was added to the reaction solution and extraction was performed with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain 133 mg of 3-benzyloxycarbonyl-8-(2-fluorophenyl)-7-oxo-3-azabicyclo[4.3.0]nonane.

Workup

  1. stirringthe mixture was stirred overnight at 100° C
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e637d37fefc74bd8b22b3ac9ed944103
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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