Ethyl 3-(4-benzyloxyphenyl)-2-aminopropionate → Ethyl 3-(4-benzyloxyphenyl)-2-(pyrrole-1-yl)propionate

HRID 1860103Notes

Reaction equation

HRID 1860103 reaction equation
Cl[CH:2](OC)[CH2:3][CH2:4][CH:5](Cl)OC.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH2:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([N:32]2[CH:5]=[CH:4][CH:3]=[CH:2]2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 4681968Ethyl 3-(4-benzyloxyphenyl)-2-aminopropionateHCID 128533161,4-Dichloro-1,4-dimethoxybutane

Product 1

HCID 18625911Ethyl 3-(4-benzyloxyphenyl)-2-(pyrrole-1-yl)propionateYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,4-dichloro-1,4-dimethoxybutane (3.30 g) was added to a solution of ethyl 3-(4-benzyloxyphenyl)-2-aminopropionate (3.30 g) in dichloromethane (80 ml) and then amberlyst A-21 (20 g) was added to the mixture. The mixture was stirred at ambient temperature for 18 hours and the reaction mixture was filtered. The filtrate was concentrated and the residue was purified via chromatography on a silica gel column using ethyl acetate/hexane=1/5 as the eluant to afford the desired compound (1.00 g) as a syrup.

Workup

  1. additionamberlyst A-21 (20 g) was added to the mixture
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-a84d82773088476f828f7fcd75eee02b
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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