HCID 14500594, compound → HCID 14500599, compound

HRID 1761603Notes

Reaction equation

HRID 1761603 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][CH2:11][CH3:12])=[CH:8][CH:7]=[C:6]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH2:23])=[O:22])[CH:15]=1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C>[CH2:1]([N:5]1[C@H:9]([CH2:10][CH2:11][CH3:12])[CH2:8][CH2:7][C@@H:6]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH2:23])=[O:22])[CH:15]=1)[CH2:2][CH2:3][CH3:4].[CH2:1]([N:5]1[C@@H:9]([CH2:10][CH2:11][CH3:12])[CH2:8][CH2:7][C@@H:6]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH2:23])=[O:22])[CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 14500594HCID 14500594, compound

Product 2

HCID 14500599HCID 14500599, compoundYield 37%HCID 14500600HCID 14500600, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3 g (90 mmol) of 1-butyl-2-(3'-ureidobenzyl)-5-propylpyrrole in 150 ml of glacial acetic acid was hydrogenated at 45 p.s.i. in the presence of 2 g of 5% rodium on activated alumina as catalyst, for 41/2 hours. The catalyst was then separated by filtration and the filtrate evaporated in vacuo. The residue was suspended in 100 ml of ethyl acetate, cooled to 0° C. and 30 ml of concentrated ammonium hydroxide was added thereto. The organic phase was separated, dried and evaporated in vacuo. The residue was purified by t.l.c. using a (50:50) mixture of chloroform-[chloroform:methanol:ammonium hydroxide (60:10:1)] as the eluant, to produce 1.1 g (37%) of the less polar cis-1-butyl-2-(3'-ureidobenzyl)-5-propylpyrrolidine isomer, and 150 mg (5%) of the more polar trans-1-butyl-2-(3'-ureidobenzyl)-5-propylpyrrolidine isomer, which was recrystallized from ether hexane.

Workup

  1. custom2 hours
  2. customThe catalyst was then separated by filtration
  3. customthe filtrate evaporated in vacuo
  4. addition30 ml of concentrated ammonium hydroxide was added
  5. customThe organic phase was separated
  6. customdried
  7. customevaporated in vacuo
  8. customThe residue was purified by t.l.c
  9. additiona (50:50) mixture of chloroform-[chloroform:methanol:ammonium hydroxide (60:10:1)] as the eluant

Sources & evidence

ORD record
ord-c645a026fe4a4c999b3b33df16604ff8
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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