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Sodium Carbonate → 1-(3,4,5-Trimethoxybenzoyl)-3-(phenylmethyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 323271
Notes
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Reaction equation

HRID 323271 reaction equation
[C:1]1([CH2:7][C:8]2([CH2:13][CH2:14][OH:15])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.O.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([O:42][CH3:43])[C:39]=1[O:40][CH3:41])[C:34](Cl)=[O:35]>C(OCC)(=O)C>[CH3:43][O:42][C:38]1[CH:37]=[C:33]([CH:32]=[C:31]([O:30][CH3:29])[C:39]=1[O:40][CH3:41])[C:34]([N:10]1[CH2:11][CH2:12][C:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)=[O:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 18464730HCID 18464730, compoundHCID 22728543Water ethylacetate

Product 1

HCID 184645521-(3,4,5-Trimethoxybenzoyl)-3-(phenylmethyl)-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

Combine 3-(phenylmethyl)-3-(2-hydroxyethyl)pyrrolidine (3.94 mmol) and sodium carbonate (0.21 g, 2.00 mmol) in 1/1 ethyl acetate/water (50 mL). Cool the reaction mixture to 0° C. with an ice bath. Add 3,4,5-trimethoxybenzoyl chloride (0.83 g, 3.58 mmol). Warm to ambient temperature. After 18 hours, separate the layers and extract the aqueous layer three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.09 (silica gel, ethyl acetate).

Workup

  1. temperatureWarm to ambient temperature
  2. customseparate the layers
  3. extractionextract the aqueous layer three times with ethyl acetate
  4. dry with materialDry the combined organic layers over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue

Sources & evidence

ORD record
ord-cd93ba56deb84177b3d8e961da8d91b1
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211199B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes