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Tetrahydrofuran → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-t-butyldimethylsilyloxypropyl)-2-oxopyrrolidine

HRID 323494
Notes
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Reaction equation

HRID 323494 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:8]1=[O:23].O1CCCC1.C([Li])(CC)C.[F:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46]Br)=[CH:44][CH:43]=1>C(OCC)(=O)C.CCCCCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:46][C:45]2[CH:48]=[CH:49][C:42]([F:41])=[CH:43][CH:44]=2)([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:8]1=[O:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 680214-Fluorobenzyl bromideHCID 220094511-(3,4,5-Trimethoxybenzyl)-3-(3-(t-butyldimethylsilyloxy)propyl)-2-oxopyrrolidineHCID 178418400CID 53628100

Product 1

HCID 184646181-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-t-butyldimethylsilyloxypropyl)-2-oxopyrrolidine

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(3-(t-butyldimethylsilyloxy)propyl)-2-oxopyrrolidine (0.71 g, 1.62 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of sec-butyl lithium (1.37 mL, 1.3 M in hexane, 1.78 mmol). After 30 minutes, add 4-fluorobenzyl bromide (0.34 g, 1.78 mmol). After 15 minutes, warm slowly to ambient temperature. After 12 hours, add water and 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.

Workup

  1. waitAfter 15 minutes
  2. temperaturewarm slowly to ambient temperature
  3. waitAfter 12 hours
  4. extractionextract three times with ethyl acetate
  5. dry with materialDry the combined organic layers over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue

Sources & evidence

ORD record
ord-b96792c495954cdcacfd5987bd81e23e
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