4-Chloroanisole → HCID 66701168, compound

HRID 1253743Notes

Reaction equation

HRID 1253743 reaction equation
CC(C)([O-])C.[Na+].[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:30]=[CH:29][C:28]([O:31][CH3:32])=[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]>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][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

Participants

7

Reactant 4

HCID 121674-ChloroanisoleHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

Product 1

HCID 66701168HCID 66701168, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Sodium t-butoxide (599 mg, 6.24 mmol, 3.0 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 1-chloro-4-methoxybenzene (389 mg, 2.08 mmol, 1.0 eq.) in toluene (25 ml) and the reaction mixture was degassed with Nitrogen. BINAP (51.8 mg, 0.083 mmol, 0.04 eq.) and Pd(OAc)2 (10 mg, 0.0416 mmol, 0.02 equiv) were added and the resulting 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; 0-10% EtOAdhexanes) to give the pure product as an oil. Yield: 35% (250 mg, 0.722 mmol).

Workup

  1. customthe reaction mixture was degassed with Nitrogen
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 16 h
  4. filtrationThe reaction mixture was filtered through celite
  5. customthe filtrate was evaporated under reduced pressure
  6. customto afford the crude product which
  7. customwas purified by column chromatography (silica gel; 0-10% EtOAdhexanes)

Sources & evidence

ORD record
ord-6b98e1ecd3654cd7bb6ac9967a23cf16
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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