1-Nitro-2-phenylethane → HCID 69015226, compound

HRID 1436525Notes

Reaction equation

HRID 1436525 reaction equation
[C:1]1([CH2:7][CH2:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH:24]([CH:25]=[O:26])[CH:23]2[CH:27]([CH2:28][O:29][CH3:30])[CH:20]1[CH2:21][CH2:22]2)=[O:18])([CH3:15])([CH3:14])[CH3:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH:24]([CH:25]([OH:26])[CH:8]([N+:9]([O-:11])=[O:10])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:23]2[CH:27]([CH2:28][O:29][CH3:30])[CH:20]1[CH2:21][CH2:22]2)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 802081-Nitro-2-phenylethaneHCID 2724141Tetrabutylammonium FluorideHCID 86615379HCID 86615379, compound

Product 1

HCID 69015226HCID 69015226, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add 1-phenyl-2-nitroethane (0.350 g, 2.23 mmol) to a solution of 3-formyl-7-methoxymethyl-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.400 g, 1.48 mmol) in anhydrous tetrahydrofaran (5 mL) cooled in an ice bath. Add tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 1.48 mL, 1.48 mmol) and stir the mixture in an ice bath for 1 h. Dilute the mixture with ethyl acetate, and wash the solution with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes) to give the title compound (0.320 g, 51%).

Workup

  1. temperaturecooled in an ice bath
  2. washwash the solution with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-8b5edb5115d5497387f327ccc684ff87
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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