Hydrochloric Acid → 3-(2,6-Difluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hexane

HRID 1814030Notes

Reaction equation

HRID 1814030 reaction equation
C(N(C(C)C)CC)(C)C.[F:10][C:11]1[CH:12]=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=[C:15]([F:18])[C:16]=1F.[CH:22]12[CH2:27][CH:26]1[CH2:25][NH:24][CH2:23]2.Cl>CN(C=O)C.C(OCC)(=O)C>[F:18][C:15]1[CH:14]=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=[C:11]([F:10])[C:16]=1[N:24]1[CH2:25][CH:26]2[CH:22]([CH2:27]2)[CH2:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27827931,2,3-Trifluoro-5-nitrobenzeneHCID 131505233-Azabicyclo(3.1.0)hexane

Product 1

HCID 114249713-(2,6-Difluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hexane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Diisopropylethylamine (0.39 mL, 2.25 mmol) and 3,4,5-trifluoronitrobenzene (0.143 g, 0.81 mmol) were added to a solution 3-aza-bicyclo[3.1.0]hexane (prepared by the general procedure of Brighty, K. E., Castaldi, M. J. Synlett, 1996, 1097-1099; 0.106 g of the HCl salt, 0.9 mmol) in DMF (2 mL). The mixture was heated for three days at 45° C. and then cooled to room temperature. The solution was diluted with ethyl acetate and washed with 0.5 M HCl, saturated NaHCO3, brine, and dried (MgSO4). The mixture was filtered and concentrated to give 3-(2,6-difluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hexane as a yellow solid.

Workup

  1. customprepared by the general procedure of Brighty, K
  2. temperaturecooled to room temperature
  3. washwashed with 0.5 M HCl, saturated NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aa6f88d54f8840a3afe87aa7abdb3a81
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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