cis-[(Methylethyl)sulfonyl][2-(4-nitrophenyl)cyclopentyl]amine → cis-[2-(4-Aminophenyl)cyclopentyl][(methylethyl)sulfonyl]amine

HRID 989500Notes

Reaction equation

HRID 989500 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 11120538cis-[(Methylethyl)sulfonyl][2-(4-nitrophenyl)cyclopentyl]amine

Product 1

HCID 59103295cis-[2-(4-Aminophenyl)cyclopentyl][(methylethyl)sulfonyl]amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(+,−) Cis propane-2-sulfonic acid [2-(4-nitro-phenyl)-cyclopentyl]-amide (200 mg, 0.64 mmol, prepared in example 22) was dissolved in 25 mL of ethanol and hydrogenated over 25 mg of 5% Pd/C at room temperature overnight at 413.69 kPa (60 psi). The solution was filtered through celite and concentrated in vacuo to 142 mg (78%) of a colorless oil which was used directly.

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated in vacuo to 142 mg (78%) of a colorless oil which

Sources & evidence

ORD record
ord-5c93a3c7d8c74f1b8a3069e4c1b1c5ee
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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