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

HRID 1993871Notes

Reaction equation

HRID 1993871 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[N+:21]([O-])=O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[NH2:21])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 66878024trans-[3-(4-Methyl-2-nitro-phenylamino)-cyclopentyl]-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 66877256trans-[3-(2-Amino-4-methyl-phenylamino)-cyclopentyl]-carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The trans-[3-(4-methyl-2-nitro-phenylamino)-cyclopentyl]-carbamic acid tert-butyl ester (320 mg, 0.95 mmol) and palladium on charcoal (10% Pd on carbon, 35 mg) in methanol (15 mL) were shaken at 52 psi of hydrogen pressure for 2.5 hours. The mixture was filtered through Celite®. Solvents were evaporated to yield trans-[3-(2-amino-4-methyl-phenylamino)-cyclopentyl]-carbamic acid tert-butyl ester as a pale brown oil (290 mg). This material (290 mg, 0.95 mmol) was dissolved in a solution (5 mL) of acetic acid and trimethyl orthoacetate (4:1 v/v). The mixture was stirred at 70° C. for 60 minutes and solvents were evaporated. The residue was extracted with ethyl acetate (25 mL) and saturated aqueous sodium bicarbonate (20 mL). The aqueous phase was again extracted with a portion of ethyl acetate and each organic phase was washed with brine. The extracts were combined, dried over sodium sulfate, filtered and evaporated to give trans-[3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester as a light brown foam (320 mg). 1H-NMR is consistent with the assigned structure. LC-MS showed a single peak, C19H27N3O2 (m/e) calcd 329.2103, obsd 330.2 (M+H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customSolvents were evaporated

Sources & evidence

ORD record
ord-67cde9f7f81b4b80bfa4089de4db4cf9
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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