Isopropyl Acetate → 5-(4-tert-Butylphenyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylic Acid Ethyl Ester

HRID 1697718

Reaction equation

HRID 1697718 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:8](/[CH:9]=[N:10]/[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br-].[Li+].C(N(CC)CC)C.[CH:28]([S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])=[CH2:29].C(OC(C)=O)(C)C>C1COCC1>[CH2:15]([O:14][C:12]([CH:11]1[CH2:29][CH:28]([S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:31])=[O:32])[CH:9]([C:8]2[CH:17]=[CH:18][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][CH:7]=2)[NH:10]1)=[O:13])[CH3:16]

Participants

7

Reactant 5

HCID 7915Isopropyl AcetateHCID 8471TriethylamineHCID 79664Phenyl vinyl sulfoneHCID 82050Lithium BromideHCID 178472689HCID 178472689, compound

Product 1

HCID 667708285-(4-tert-Butylphenyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylic Acid Ethyl EsterYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (E)-ethyl 2-(4-tert-butylbenzylideneamino)acetate (226 mg, 914 umol; example 441a) in THF (5 ml) under an argon atmosphere were added lithium bromide (119 mg, 1.37 mmol), triethylamine (191 ul, 1.37 mmol) and phenyl vinyl sulfone (154 mg, 914 umol; CAS Reg. No. 5535-48-8). The mixture was stirred at ambient temperature for 20 h. iPrOAc (50 ml) and ice water (40 ml) were added and the layers were separated. The organic layer was washed with brine (40 ml), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, iPrOAc/n-heptane) to obtain the title compound (56 mg, 73 umol; 8%) as colorless solid. MS (ESI): m/z=416.2 [M+H]

Workup

  1. additionwere added
  2. customthe layers were separated
  3. washThe organic layer was washed with brine (40 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customto give a yellow oil which
  8. customwas purified by column chromatography (silica gel, iPrOAc/n-heptane)

Sources & evidence

ORD record
ord-4a5887a39fce47c6962960c891c32db4
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Linked notes

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