Potassium Carbonate → HCID 54066569, compound

HRID 1683105Notes

Reaction equation

HRID 1683105 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:14][CH2:15][OH:16])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH2:23]([O:25][C:26]1[CH:34]=[CH:33][C:29](C(Cl)=O)=[C:28]([O:35][CH2:36][CH3:37])[C:27]=1[O:38][CH2:39][CH3:40])[CH3:24]>C(OCC)(=O)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:14][CH2:15][OH:16])[CH2:13][CH2:12][N:11]([C:17](=[O:20])[C:33]3[CH:29]=[C:28]([O:35][CH2:36][CH3:37])[C:27]([O:38][CH2:39][CH3:40])=[C:26]([O:25][CH2:23][CH3:24])[CH:34]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 184644272-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanolHCID 22117942HCID 22117942, compound

Product 1

HCID 54066569HCID 54066569, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 22728543Water ethylacetateSolvent

Procedure

Combine 3-(3,4-dichloro-phenyl)-3-(2-hydroxy-ethyl)-pyrrolidine (260 mg, 1 mmol) and and potassium carbonate (0.69 g, 5 mmol) in ethyl acetate/water (10 mL/10 mL). Cool in an ice-bath. Add a solution of triethoxy-benzoyl chloride (1.2 mmol) in ethyl acetate (10 mL). After 1 hour, dilute with ethyl acetate and extract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound: Rf =0.43 (silica gel, 6% methanol/dichloromethane).

Workup

  1. temperatureCool in an ice-bath
  2. extractionextract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-8dee561afa794316ace23afc93d72581
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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