Putrescine → HCID 21962567, compound

HRID 2211810Notes

Reaction equation

HRID 2211810 reaction equation
NCCCCN.Br[CH2:8][C:9]1[CH:28]=[CH:27][C:12]2[N:13]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:14](=[O:17])[CH2:15][O:16][C:11]=2[CH:10]=1.C[Si](Cl)(C)C.[C:34]([O:44][CH2:45][CH3:46])(=[O:43])[CH:35]=[CH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Cl-].[NH4+].[OH-].[NH4+]>O1CCCC1.[Cu]I>[O:17]=[C:14]1[N:13]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:12]2[CH:27]=[CH:28][C:9]([CH2:8][CH:36]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:35][C:34]([O:44][CH2:45][CH3:46])=[O:43])=[CH:10][C:11]=2[O:16][CH2:15]1

Participants

9

Reactant 6

HCID 1045PutrescineHCID 6397ChlorotrimethylsilaneHCID 7649Ethyl 3-phenylprop-2-enoateHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 21962583HCID 21962583, compound

Product 1

HCID 21962567HCID 21962567, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of CuI in dry tetrahydrofuran under argon are added 1.1 equivalents of tetramethylene diamine and the reaction mixture stirred at room temperature for 15 minutes. The solution is cooled to −78° C. and the Grignard reagent prepared from 7-bromomethyl-4-p-methoxybenzyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine is added and the reaction mixture stirred for 15 minutes. Then, 2 equivalents of trimethylsilyl chloride and a solution of ethyl cinnamate in tetrahydrofuran are added and the reaction mixture is stirred while the temperature is allowed to rise to −30° C. After 18 hours the reaction is poured into a solution of ammonium chloride and ammonium hydroxide and extracted with dichloromethane. The extracts are washed with water, dried over sodium sulfate, evaporated and the product isolated by flash chromatography.

Workup

  1. temperatureThe solution is cooled to −78° C.
  2. additionis added
  3. stirringthe reaction mixture stirred for 15 minutes
  4. stirringthe reaction mixture is stirred while the temperature
  5. customto rise to −30° C
  6. extractionextracted with dichloromethane
  7. washThe extracts are washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customthe product isolated by flash chromatography

Sources & evidence

ORD record
ord-0663fc22646342e5bf7a15af962162c9
Source dataset
uspto-grants-2006_09
Patent number
US07101876B2

Reaction notes

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