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

HRID 323262
Notes
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Reaction equation

HRID 323262 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 184647721-(3,4,5-Trimethoxybenzyl)-3-(phenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidine

Product 1

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

Reagents, catalysts & solvents

1
HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c8721eb2bb0f4b058c7a0746d73cacdf
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211199B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes