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

HRID 323429노트

반응식

HRID 323429 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매2회HCID 21226206Ethyl acetate hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-401d2abe422342a5a74ab9324ab3f15a
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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