Cesium carbonate → HCID 66700783, compound

HRID 1253742Notes

Reaction equation

HRID 1253742 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10][CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].Cl[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:14]2[CH2:13][CH2:12][C:11]3([CH2:7][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9][CH2:10]3)[CH2:16][CH2:15]2)=[CH:26][CH:27]=1)#[N:30]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 121634-ChlorobenzonitrileHCID 634876Binap, (A+-)-HCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

Product 1

HCID 66700783HCID 66700783, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Cesium carbonate (1.35 g, 4.16 mmol, 2.0 eq.) was added to a stirred solution of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (500 mg, 2.08 mmol, 1.0 eq.) and 4-chlorobenzonitrile (390 mg, 2.08 mmol, 1.0 eq.) in toluene (30 ml) and the reaction mixture was degassed with nitrogen for 15 min. BINAP (52 mg, 0.083 mmol, 0.04 eq.) and Pd(OAc)2 (10 mg, 0.0416 mmol, 0.02 eq.) were added and the resulting reaction mixture was heated at reflux for 16 h. The reaction mixture was filtered through celite and the filtrate was evaporated under reduced pressure to afford the crude product which was purified by column chromatography (silica gel; 15-20% EtOAdhexanes) to yield the pure product as an oil. Yield: 49% (350 mg, 1.026 mmol).

Workup

  1. customthe reaction mixture was degassed with nitrogen for 15 min
  2. customthe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 16 h
  5. filtrationThe reaction mixture was filtered through celite
  6. customthe filtrate was evaporated under reduced pressure
  7. customto afford the crude product which
  8. customwas purified by column chromatography (silica gel; 15-20% EtOAdhexanes)

Sources & evidence

ORD record
ord-46a74349f4ea4eda851c671056462087
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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