Sodium Carbonate → 1-(2-Methoxy-5-trifluoromethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 323429Notes

Reaction equation

HRID 323429 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.[C:31]1([C:37]2([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][NH:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:51][O:52][C:53]1[CH:61]=[CH:60][C:59]([O:62][C:63]([F:66])([F:65])[F:64])=[CH:58][C:54]=1[C:55](Cl)=[O:56]>C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>[CH3:51][O:52][C:53]1[CH:61]=[CH:60][C:59]([O:62][C:63]([F:64])([F:65])[F:66])=[CH:58][C:54]=1[C:55]([N:39]1[CH2:40][CH2:41][C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([CH2:42][CH2:43][OH:44])[CH2:38]1)=[O:56]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 35805962-Methoxy-5-(trifluoromethoxy)benzoyl chlorideHCID 70109704(-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

Product 1

HCID 220094081-(2-Methoxy-5-trifluoromethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (1.7 g, 2.5 mmol) and sodium carbonate (1.32 g, 12.5 mmol) in ethyl acetate/water (1/1) (20 mL). Add a solution of 2-methoxy-5-trifluoromethoxybenzoyl chloride (0.64 g, 2.5 mmol) in ethyl acetate (10 mL). After 14 hours, separate the organic layer. Extract the aqueous layer four times with dichloromethane. 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=0.32 (silica gel, ethyl acetate).

Workup

  1. customseparate the organic layer
  2. extractionExtract the aqueous layer four times with dichloromethane
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-401d2abe422342a5a74ab9324ab3f15a
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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