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Hydrochloric Acid → 1-(3,4,5-Trimethoxybenzyl)-3-(phenylmethyl)-3-(2-hydroxyethyl)-2-oxopyrrolidine

HRID 323262
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HRID 323262 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C)C)[C:8]1=[O:29].O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C(OCC)(=O)C.CCCCCC>[CH3:36][O:35][C:31]1[CH:30]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:32]=1[O:33][CH3:34])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([CH2:12][CH2:13][OH:14])[C:8]1=[O:29]
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HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 184647721-(3,4,5-Trimethoxybenzyl)-3-(phenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidine

생성물 1

HCID 184644501-(3,4,5-Trimethoxybenzyl)-3-(phenylmethyl)-3-(2-hydroxyethyl)-2-oxopyrrolidine

시약·촉매·용매 1

HCID 21226206
Ethyl acetate hexane
용매

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온도
0 °C

실험 절차

Combine 1-(3,4,5-trimethoxybenzyl)-3-(phenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidine (1.0 g, 1.95 mmol) and tetrahydrofuran (5 mL). Cool to 0° C. using a ice bath. Add a solution of tetrabutylammonium fluoride (3.90 mL, 1 M in THF, 3.90 mmol). After the addition is complete, warm to ambient temperature. After 1.5 hours, add aqueous 1 M hydrochloric acid solution (20 mL). Extract three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give the title compound: Rf=0.27 (silica gel, 1/1 ethyl acetate/hexane).

후처리

  1. additionAfter the addition
  2. temperaturewarm to ambient temperature
  3. extractionExtract three times with ethyl acetate
  4. dry with materialDry the combined organic layers over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue

출처 및 근거

ORD 기록
ord-c8721eb2bb0f4b058c7a0746d73cacdf
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211199B1

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