Benzylamine → 1-Benzyl-2,5-dihydropyrrole

HRID 1058942Notes

Reaction equation

HRID 1058942 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]\[CH2:5]Cl.[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:7]([N:14]1[CH2:5][CH:4]=[CH:3][CH2:2]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 5615061-Benzyl-2,5-dihydropyrrole

Procedure

A mixture of 1,4-dichloro-cis-2-butene and benzylamine is heated at reflux to give 1-benzyl-3-pyrroline (2), which is converted to the epoxide (3) by first reacting (2) with chlorine in dilute hydrochloric acid and then with sodium hydroxide. The epoxide is opened to give the corresponding hydroxy amine (4) with either ammonia and water or sodium azide followed by reduction of the resulting azide. The resulting trans 1-benzyl-3-amino-4-hydroxypyrrolidine (4) is acetylated with acetic anhydride to give N-acetyl derivative (5) in which N-benzyl group is removed by hydrogenation in the presence of Pd/C under acidic conditions to give (6), and further alkylated with bromoethyl acetate to give N-ethoxycarbonyl methyl derivative (7). The basic hydrolysis of the ester (7) gives the target (8).

Workup

  1. temperatureis heated
  2. temperatureat reflux

Sources & evidence

ORD record
ord-578b7e7393434c3396ebb1aff4248f11
Source dataset
uspto-grants-2003_02
Patent number
US06518299B1

Reaction notes

Loading…