1-Nitropropane → HCID 86586528, compound

HRID 1357785Notes

Reaction equation

HRID 1357785 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH:26]=O)=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N+:28]([CH2:31][CH2:32][CH3:33])([O-:30])=[O:29].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[N+:23]([C:20]1[CH:21]=[CH:22][C:16]2[O:15][CH2:14][CH:13]([CH2:12][O:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[O:18][C:17]=2[C:19]=1[CH:26]=[C:31]([N+:28]([O-:30])=[O:29])[CH2:32][CH3:33])([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 79031-NitropropaneHCID 517165Ammonium AcetateHCID 12082209HCID 12082209, compound

Product 1

HCID 86586528HCID 86586528, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1.0 g (2.45 mmole) of (2R)-(8-formyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl 4-methylbenzenesulfonate in 15 mL of acetic acid was added 0.87 mL (9.8 mmole) of nitropropane and 0.38 g (4.9 mmole) of ammonium acetate and the mixture was heated at 80° C. under nitrogen for 6 hours. After the mixture cooled, the solvent was removed in vacuum and replaced with 200 mL of ethyl acetate. The solution was washed with 200 mL of water and the aqueous wash was back-extracted with an additional 200 mL of ethyl acetate. The combined organics were washed with 200 mL each of saturated aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuum to an oily yellow solid. Column chromatography on silica gel with 1:1 hexane/ethyl acetate as eluant gave 0.70 g of the (R)-enantiomer of the title compound as a yellow solid. 1H-NMR (CDCl3): doublet 7.8 δ (2 H); doublet 7.75 δ (1 H); doublet 7.4 δ (2 H); doublet 7.03 δ (1 H); singlet 5.3 δ (1 H); multiplet 4.45 δ (1 H); multiplet 4.4 δ (1 H); multiplet 4.21 δ (3 H); singlet 2.45 δ (3 H); quartet 2.4 δ (2 H); triplet 1.0 δ (3 H).

Workup

  1. temperatureAfter the mixture cooled
  2. customthe solvent was removed in vacuum
  3. washThe solution was washed with 200 mL of water
  4. washthe aqueous wash
  5. extractionwas back-extracted with an additional 200 mL of ethyl acetate
  6. washThe combined organics were washed with 200 mL each of saturated aqueous sodium bicarbonate and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuum to an oily yellow solid

Sources & evidence

ORD record
ord-6fe41d565e60444ca4321fa93fded5d5
Source dataset
uspto-grants-2003_07
Patent number
US06593350B2

Reaction notes

Loading…