Acetonitrile → 1-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 1682961Notes

Reaction equation

HRID 1682961 reaction equation
C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=O)C1C=CC(OC)=CC=1.[Cl:31][C:32]1[CH:33]=[C:34]([C:39]2([CH2:44][CH2:45][OH:46])[CH2:43][CH2:42][NH:41][CH2:40]2)[CH:35]=[CH:36][C:37]=1[Cl:38].C(#N)C.[C:50](=[O:53])(O)[O-].[Na+].[CH3:55][O:56][C:57]1[CH:65]=[CH:64][C:60]([C:61](Cl)=[O:62])=[C:59](OC)[C:58]=1[O:68][CH3:69]>O>[CH3:69][O:68][C:58]1[CH:59]=[C:60]([CH:64]=[C:65]([O:53][CH3:50])[C:57]=1[O:56][CH3:55])[C:61]([N:41]1[CH2:42][CH2:43][C:39]([C:34]2[CH:35]=[CH:36][C:37]([Cl:38])=[C:32]([Cl:31])[CH:33]=2)([CH2:44][CH2:45][OH:46])[CH2:40]1)=[O:62]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 27608082,3,4-trimethoxybenzoyl chlorideHCID 131720034HCID 131720034, compound

Product 1

HCID 184644171-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Combine (+)-3-(3,4-dichloro-phenyl)-3-(2-hydroxyethyl)-pyrrolidine (R, R)-di-p-anisoyltartaric acid salt (0.14 g, 0.21 mmol) ethyl acetate (15 mL, acetonitrile (6 mL), water, (6 mL) and sodium bicarbonate (0.09 g, 1.03 mmol). Cool to 0° C. in an ice-salt bath. Add trimethoxybenzoyl chloride (0.048 g, 0.21 mmol). After 30 minutes, warm to ambient temperature. After 30 minutes at ambient temperature, partition the reaction mixture between ethyl acetate and saturated aqueous sodium chloride solution. Extract the organic layer with 1M hydrochloric acid solution, then saturated aqueous sodium bicarbonate solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound: Rf =0.11 (silica gel, ethyl acetate).

Workup

  1. temperaturewarm to ambient temperature
  2. waitAfter 30 minutes at ambient temperature
  3. custompartition the reaction mixture between ethyl acetate and saturated aqueous sodium chloride solution
  4. extractionExtract the organic layer with 1M hydrochloric acid solution
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-308b7cd19d0143cfb38857b625d0ec35
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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