Nitromethane → HCID 54315857, compound

HRID 498117Notes

Reaction equation

HRID 498117 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@H:9]1[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18]N(C)C(=N)N(C)C.[N+:26]([CH3:29])([O-:28])=[O:27]>>[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@H:9]1[CH:11]([CH2:18][CH2:29][N+:26]([O-:28])=[O:27])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-Tetramethylguanidine2×HCID 54062723HCID 54062723, compound

Product 1

HCID 54315857HCID 54315857, compoundYield 85.9%

Procedure

To 60 ml of a nitromethane solution of 6.07 g (25.2 mmol) of ethyl 3-(cis-2-t-butoxycarbonylcyclopropyl)-acrylate was added 3.48 ml (27.7 mmol) of tetramethylguanidine at room temperature, and the mixture was stirred for 6 hours. To the reaction mixture was further added 0.32 ml (2.52 mmol) of tetramethylguanidine, followed by stirring for 18 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15) to give 6.536 g (85.9%) of the title compound as a pale yellow oily substance.

Workup

  1. stirringby stirring for 18 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-64c9be27d63d4d188145d4327745d20a
Source dataset
uspto-grants-2005_09
Patent number
US06949662B2

Reaction notes

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