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Benzoyl chloride → 1-Benzoyl-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 323403
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HRID 323403 반응식
[C:1]([C@](C(O)=O)(O)[C@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5](OC)=[CH:4][CH:3]=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(OCC)(=O)C.CCCCCC.C(=O)(O)[O-].[Na+].C(Cl)(=O)C1C=CC=CC=1>CC(C)=O.ClCCl.CO>[C:1]([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:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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7

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HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 70109704(-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

생성물 1

HCID 184650691-Benzoyl-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

시약·촉매·용매 2

HCID 180
Acetone
용매
HCID 21226129Dichloromethane methanol용매

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온도
0 °C

실험 절차

Combine (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (11.1 g, 18.3 mmol) and acetone/water (1/1, 200 mL). Cool to about 0° C. in an ice bath and add sodium bicarbonate (10.6 g, 217.6 mmol). Warm to ambient temperature and slowly add a solution of benzoyl chloride (4.2 g, 365 mmol) in acetone (10 mL). After 18 hours, filter and dilute the filtrate with ethyl acetate. Extract the diluted filtrate with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with dichloromethane/methanol 95/5 to give the title compound: Rf=0.81 (silica gel, dichloromethane/methanol 95/5).

후처리

  1. temperatureWarm to ambient temperature
  2. filtrationfilter
  3. additiondilute the filtrate with ethyl acetate
  4. extractionExtract the diluted filtrate with a saturated aqueous sodium bicarbonate solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

출처 및 근거

ORD 기록
ord-28767a038a794a32816f96fd47d06306
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211199B1

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