N,N'-Dimethylethylenediamine → Tert-butyl 3-[4-(methoxycarbonyl)phenyl]-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylate

HRID 402754Notes

Reaction equation

HRID 402754 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[O:7]=[C:8]1[NH:12][CH2:11][C:10]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[O:9]1.CNCCNC.Br[C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1>[Cu]I>[CH3:39][O:38][C:36]([C:35]1[CH:40]=[CH:41][C:32]([N:12]2[CH2:11][C:10]3([CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]3)[O:9][C:8]2=[O:7])=[CH:33][CH:34]=1)=[O:37]

Participants

6

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 12081Methyl 4-bromobenzoateHCID 10015278Tert-butyl 2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66766106Tert-butyl 3-[4-(methoxycarbonyl)phenyl]-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A mixture of cesium carbonate (4.27 g, 13.11 mmol), copper (I) iodide (0.832 g, 4.37 mmol), tert-butyl 2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylate (1.12 g, 4.37 mmol), N,N′-dimethylethane-1,2-diamine (0.385 g, 437 mmol) and methyl 4-bromobenzoate (1.128 g, 5.24 mmol) was heated under nitrogen for 18 hours. The crude mixture was filtered through celite. Upon removal of the volatiles, the crude was purified by flash chromatography (EtOAc/hexanes 20 to 100%) to afford the title intermediate as a white solid.

Workup

  1. temperaturewas heated under nitrogen for 18 hours
  2. filtrationThe crude mixture was filtered through celite
  3. customUpon removal of the volatiles
  4. customthe crude was purified by flash chromatography (EtOAc/hexanes 20 to 100%)

Sources & evidence

ORD record
ord-38fd7385194746d3be58d6c32e42447c
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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