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1-Pyrrolidineethanol → HCID 69209252, compound

HRID 2221166
Notes
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Reaction equation

HRID 2221166 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([C:20]2[O:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[CH:21]=2)[C:14](=[O:19])[CH:15]=[CH:16][CH2:17]Br)=[CH:6][CH:5]=1.O.[OH-].[OH:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(=O)OCC>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([C:20]2[O:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[CH:21]=2)[C:14](=[O:19])[CH:15]=[CH:16][CH2:17][O:32][CH2:33][CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 762881-PyrrolidineethanolHCID 445487Hydroxide, hydrateHCID 69206561HCID 69206561, compound

Product 1

HCID 69209252HCID 69209252, compoundYield 0.3%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalyst
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[2-(3-benzofuran-2-yl-4-bromobut-2-enoylamino)ethoxy]benzoic acid methyl ester (300 mg, 0.654 mmol) in dry DMF (4 ml), cessium hydroxide monohydrate (121 mg, 0.72 mmol), tetrabutylammonium iodide (49 mg, 0.13 mmol) and 1-(2-hydroxy-ethyl)pyrrolidine (85 ul, 0.72 mmol) were added. The reaction mixture was stirred overnight at rt and then diluted with EA (20 ml) and washed with water and brine. After drying over sodium sulfate, the solvent was evaporated under vacuum and the crude was purified on preparative TLC, DCM/MeOH (9/1) to give 4-{2-[3-benzofuran-2-yl-4-(2-pyrrolidin-1-yl-ethoxy)but-2-enoylamino]ethoxy}benzoic acid methyl ester (0.94 mg) as an oil.

Workup

  1. washwashed with water and brine
  2. dry with materialAfter drying over sodium sulfate
  3. customthe solvent was evaporated under vacuum
  4. customthe crude was purified on preparative TLC, DCM/MeOH (9/1)

Sources & evidence

ORD record
ord-6257d0facfd54f5a81f3c31c5b18d50b
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368476B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes