HCID 14500608, compound → HCID 14500610, compound

HRID 1761604Notes

Reaction equation

HRID 1761604 reaction equation
[CH2:1]([N:4]1[C:8]([CH2:9][CH2:10][CH3:11])=[CH:7][CH:6]=[C:5]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([NH2:22])=[O:21])[CH:14]=1)[CH2:2][CH3:3]>C(O)(=O)C>[CH2:1]([N:4]1[C@H:8]([CH2:9][CH2:10][CH3:11])[CH2:7][CH2:6][C@@H:5]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([NH2:22])=[O:21])[CH:14]=1)[CH2:2][CH3:3].[CH2:1]([N:4]1[C@@H:8]([CH2:9][CH2:10][CH3:11])[CH2:7][CH2:6][C@@H:5]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([NH2:22])=[O:21])[CH:14]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 14500608HCID 14500608, compound

Product 2

HCID 14500610HCID 14500610, compoundYield 39%HCID 14500611HCID 14500611, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4.6 g (15 mmol) of 1,5-dipropyl-2-(3'-ureidobenzyl)pyrrole in 150 ml of glacial acetic acid was hydrogenated at 45 p.s.i. in the presence of 3.5 g of 5% rodium on activated alumina as catalyst, during 2 hours. The catalyst was then separated by filtration and the filtrate evaporated in vacuo. The residue was suspended in 100 ml of methylene chloride and 20 ml of ammonium hydroxide were added (to adjust pH to alkaline). Anhydrous sodium sulfate was added and the solvent evaporated under reduced pressure. The residue was purified by t.l.c. using an (80:20) mixture of chloroform [chloroform-methanol-ammonium hydroxide (60:10:1)] as the eluant, thus obtaining 1.83 g (39%) of the less polar cis-1,5-dipropyl-2-(3'-ureidobenzyl)pyrrolidine isomer (as an oil), and 214 mg (5%) of the more polar trans-1,5-dipropyl-2-(3'-ureidobenzyl)pyrrolidine isomer, which was recrystallized from ether-hexane.

Workup

  1. customThe catalyst was then separated by filtration
  2. customthe filtrate evaporated in vacuo
  3. addition20 ml of ammonium hydroxide were added (to adjust pH to alkaline)
  4. additionAnhydrous sodium sulfate was added
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by t.l.c
  7. additionan (80:20) mixture of chloroform [chloroform-methanol-ammonium hydroxide (60:10:1)] as the eluant

Sources & evidence

ORD record
ord-3a378bca268e484684030e3b550a806e
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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