Butylamine → 4-Butylamino-5-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxlic acid tert-butyl ester

HRID 457429Notes

Reaction equation

HRID 457429 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[C:14]([N+:20]([O-])=O)=[CH:15][C:16]=32)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:26](N)[CH2:27][CH2:28][CH3:29]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[C:14]([NH:20][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:15][C:16]=32)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 8007ButylamineHCID 53923553HCID 53923553, compound

Product 1

HCID 690303734-Butylamino-5-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxlic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (500 mg, 1.43 mmol) and 1-butylamine (1.42 mL, 14.3 mmol) were combined in THF (5 mL) and stirred 4 hours. The mixture was diluted with ethyl acetate (50 mL) and washed with H2O (3×30 mL) then dried (Na2SO4), filtered and concentrated to an oil. This oil was passed through a Silica gel filter column to remove baseline impurities eluting with 30% ethyl acetate/hexanes (510 mg, 1.41 mmol, 99%).

Workup

  1. washwashed with H2O (3×30 mL)
  2. dry with materialthen dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. filtrationfilter column
  6. customto remove baseline impurities

Sources & evidence

ORD record
ord-f8b48683713b4d4fa2902c6c103f1cf0
Source dataset
uspto-grants-2007_03
Patent number
US07186870B2

Reaction notes

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