Potassium Carbonate → trans-[3-(4-Methyl-2-nitro-phenylamino)-cyclopentyl]-carbamic acid tert-butyl ester

HRID 1993870Notes

Reaction equation

HRID 1993870 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].F[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1362874-Fluoro-3-nitrotolueneHCID 45091937tert-Butyl N-((1S,3S)-3-aminocyclopentyl)carbamate

Product 1

HCID 66878024trans-[3-(4-Methyl-2-nitro-phenylamino)-cyclopentyl]-carbamic acid tert-butyl esterYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

The trans-(3-amino-cyclopentyl)-carbamic acid tert-butyl ester (420 mg, 2.09 mmol) was mixed with 4-fluoro-3-nitrotoluene (342 mg, 2.2 mmol) and potassium carbonate (915 mg, 6.6 mmol) in DMF (20 mL). The stirring mixture was heated at 85° C. for 16.5 hours. The reaction mixture was evaporated under reduced pressure. The residue was partitioned with 50 mL of dichloromethane and 50 mL of brine. The aqueous phase was extracted again with 50 mL of dichloromethane and each organic extract was washed with a portion of brine. After drying, filtering and evaporation of solvents, the crude mixture was purified on silica gel eluting with ethyl acetate and hexanes to give trans-[3-(4-methyl-2-nitro-phenylamino)-cyclopentyl]-carbamic acid tert-butyl ester as a orange oil (305 mg). 1H-NMR is consistent with the assigned structure. LC-MS showed a single peak, C17H25N3O4 (m/e) calcd 335.1845, obsd 336.2 (M+1).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customThe residue was partitioned with 50 mL of dichloromethane and 50 mL of brine
  3. extractionThe aqueous phase was extracted again with 50 mL of dichloromethane
  4. extractioneach organic extract
  5. washwas washed with a portion of brine
  6. customAfter drying
  7. filtrationfiltering
  8. customevaporation of solvents
  9. customthe crude mixture was purified on silica gel eluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-d3dadfe186d64242be14b99f5436f11d
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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