Cesium carbonate → HCID 59813962, compound

HRID 2115296Notes

Reaction equation

HRID 2115296 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][C:11]2([C:15](=[O:16])[NH:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27][CH3:28])[CH:21]=1.CN(C)CCN.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I.CCOC(C)=O.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:15](=[O:16])[N:14]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27][CH3:28])[CH:21]=3)[CH2:13][CH2:12]2)[CH2:17][CH2:18]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 66053N,N-DimethylethylenediamineHCID 27695675-Bromo-2-chloroanisoleHCID 45073946tert-Butyl 1-oxo-2,8-diazaspiro(4.5)decane-8-carboxylate

Product 1

HCID 59813962HCID 59813962, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-oxo-2,8-diaza-spiro[4,5]decane-8-carboxylic acid tert-butyl ester (127 mg, 0.5 mmol, 1 equiv), 4-bromo-1-chloro-2-methoxy-benzene (221 mg, 2equiv), N,N-dimethylethylenediamine (14 mg, 0.3 equiv), CuI (29 mg, 0.3 equiv) and Cs2CO3 (325 mg, 2 equiv) in 1 mL of dioxane were heated at 110° C. overnight and then cooled to room temperature, taken up in a 1:1 mixture of methanol and EtOAc, filtered through a thin pad of celite and concentrated. The crude product was purified by flash column to give 2-(4-Chloro-3-methoxy-phenyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a thin pad of celite
  3. concentrationconcentrated
  4. customThe crude product was purified by flash column

Sources & evidence

ORD record
ord-9c8d565603874720abfc7f05ecab02f0
Source dataset
uspto-grants-2008_10
Patent number
US07435831B2

Reaction notes

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