Nitromethane → HCID 131728908, compound

HRID 551658Notes

Reaction equation

HRID 551658 reaction equation
[CH:1]1([C:6]2[CH2:7][C@@H:8]3[C@H:11]([CH:12]=2)[C:10](=[CH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.P([O-])(O)(O)=O.[K+].[N+:38]([CH3:41])([O-:40])=[O:39]>>[N+:38]([CH2:41][C@@:10]1([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][C@H:8]2[C@@H:11]1[CH:12]=[C:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:7]2)([O-:40])=[O:39]

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516951Monobasic potassium phosphateHCID 131728907HCID 131728907, compound

Product 1

HCID 131728908HCID 131728908, compound

Conditions

Temperature
60 °C

Procedure

Tert-butyl(±)-[(1S,5R)-3-cyclopentylbicyclo[3.2.0]hept-3-en-6-ylidene]acetate (3.30 g, 12.0 mmol) was dissolved in nitromethane (30 mL). To the solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.20 g, 14.5 mmol) was added, and the mixture was stirred at 60° C. for 5 hours. The mixture was allowed to cool, and a saturated aqueous solution of potassium dihydrogen phosphate was then added thereto, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain the compound of interest as a yellow oil substance (3.50 g, 87%).

Workup

  1. temperatureto cool
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel chromatography
  6. customto obtain the compound of interest as a yellow oil substance (3.50 g, 87%)

Sources & evidence

ORD record
ord-f263541449854ea0bb1741cad83bba81
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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