p-Bromomandelic acid → HCID 67541966, compound

HRID 2355835Notes

Reaction equation

HRID 2355835 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=O)=[CH:4][CH:3]=1.COC1C=[C:29]([CH:33]2C[CH2:36][CH2:35][NH:34]2)[CH:30]=[CH:31][CH:32]=1.OC(C1C=CC(Br)=CC=1)C(O)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:36][CH2:35][N:34]4[CH2:33][CH2:29][CH2:30][CH2:31][CH2:32]4)=[CH:19][CH:20]=3)[C@@H:12]3[CH2:13][CH2:14][CH2:15][N:11]3[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 97930p-Bromomandelic acidHCID 36138242-(3-Methoxyphenyl)pyrrolidineHCID 67542421HCID 67542421, compound

Product 1

HCID 67541966HCID 67541966, compound

Procedure

2-(4-Bromo-phenyl)-2-hydroxy-1-[2-(3-methoxy-phenyl)-pyrrolidin-1-yl]-ethanone. A solution of 2-(3-methoxy-phenyl)-pyrrolidine (16.9 mmol, 1.0 equiv.) and hydroxy-(4-bromo-phenyl)-acetic acid (1.0 equiv.) in xylenes (0.2 M) was heated at reflux for 3 d under nitrogen. The bulk of the xylenes was removed by distillation and the residue was purified by chromatography (EtOAc/hexanes) to give the desired product as a mixture of diastereomers (3.66 g, 55%). MS: exact mass calcd for C19H20BrNO3, 389.1; m/z found, 390.0 [M+H]+, 392.0 [M+H]+.

Workup

  1. temperatureat reflux for 3 d under nitrogen
  2. customThe bulk of the xylenes was removed by distillation
  3. customthe residue was purified by chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-a30e3e34601a4fa8beba42997e374485
Source dataset
uspto-grants-2010_07
Patent number
US07754882B2

Reaction notes

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