Nitromethane → HCID 86722944, compound

HRID 1404336Notes

Reaction equation

HRID 1404336 reaction equation
C(N1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2)C(C)C.[N+:24]([CH3:27])([O-:26])=[O:25].[CH2:28]([O:30][C:31](=[O:48])[CH:32]=[C:33]1[CH2:38][CH2:37][CH:36]([CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:34]1)[CH3:29]>C1COCC1>[CH2:28]([O:30][C:31](=[O:48])[CH2:32][C:33]1([CH2:27][N+:24]([O-:26])=[O:25])[CH2:38][CH2:37][CH:36]([CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:34]1)[CH3:29]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 86722941HCID 86722941, compound

Product 1

HCID 86722944HCID 86722944, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A sealable reaction tube was charged with 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.16 mL, 0.450 mmol) and THF (1.0 mL) under Argon. Nitromethane (0.23 mL, 4.24 mmol) was added and the reaction stirred at room temperature for 5 min then cooled to 0° C. for 15 min. [4-(tert-Butoxycarbonylamino-methyl)-cyclohexylidene]-acetic acid ethyl ester (0.261 g, 0.878 mmol) in THF (1.5 mL) was added slowly and the reaction stirred at RT for 15 min. The tube was sealed and the reaction heated at 70° C. for 17 hr. The reaction was cooled to room temperature, quenched with 0.5M HCl, and extracted with EtOAc (2×). The combined organic layers were washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated to provide 0.304 g of crude product which was carried to the next step without purification. ESI-MS m/z 359 (MH)+.

Workup

  1. additionwas added slowly
  2. stirringthe reaction stirred at RT for 15 min
  3. customThe tube was sealed
  4. temperaturethe reaction heated at 70° C. for 17 hr
  5. temperatureThe reaction was cooled to room temperature
  6. customquenched with 0.5M HCl
  7. extractionextracted with EtOAc (2×)
  8. washThe combined organic layers were washed with saturated NaHCO3 and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d0c81e8913ce4199942d9790da2bd3e5
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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