Tosylmethyl isocyanide → methyl 4-(4-methoxy-4-oxobutyl)-1H-pyrrole-3-carboxylate

HRID 872187Notes

Reaction equation

HRID 872187 reaction equation
[Li]N([Si](C)(C)C)[Si](C)(C)C.CC1C=CC(S([CH2:21][N+:22]#[C-:23])(=O)=O)=CC=1.[C:24]([O:35][CH3:36])(=[O:34])/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31]>C1COCC1>[CH3:36][O:35][C:24](=[O:34])[CH2:25][CH2:26][CH2:27][C:28]1[C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:21][NH:22][CH:23]=1

Participants

5

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 64295883-Methyl-hept-2-enedioic acid dimethyl ester, EHCID 178418261HCID 178418261, compound

Product 1

HCID 68276464methyl 4-(4-methoxy-4-oxobutyl)-1H-pyrrole-3-carboxylateYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a 1 M solution of LiN(TMS)2 in THF (5.9 mL, 5.9 mmol) cooled at −78° C. under argon was added a solution of TOSMIC (1.15 g, 5.9 mmol) in THF (15 mL) dropwise. After 40 min at −78° C. a solution of dimethyl (2E)-hept-2-enedioate (1.1 g, 5.9 mmol) in THF (15 mL) at −78° C. was added slowly. The solution was stirred for 10 min, then the cold bath was removed and the reaction was allowed to warm at room temperature. THF was evaporated and the residue partioned between H2O (200 mL) and DCM (200 mL). Aqueous layer was extracted with DCM and the combined organic layers anidrified on Na2SO4, filtered and concentrated to give a residue which was chromatographed on silica gel (eluant: AcOEt/hexane 3/7) to afford 633 mg (yield: 40%) of the title compound as white solid.

Workup

  1. customthe cold bath was removed
  2. customTHF was evaporated
  3. extractionAqueous layer was extracted with DCM
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas chromatographed on silica gel (eluant: AcOEt/hexane 3/7)

Sources & evidence

ORD record
ord-4b7e264de72b427282c950bf77467a42
Source dataset
uspto-grants-2015_03
Patent number
US08975267B2

Reaction notes

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