Tosylmethyl isocyanide → methyl 4-(4-methoxy-4-oxobutyl)-1H-pyrrole-3-carboxylate
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]=1Participants
Procedure
To a 1 M solution of LiN(TMS)2 in THF (5.9 mL, 5.9 mmol) cooled ate −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) Acqueous layer was extracted with DCM and the combined organic layers anidrified on Na2SO4, filtered and concentred 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
- customate −78° C. under argon
- customthe cold bath was removed
- customTHF was evaporated
- extractionthe residue partioned between H2O (200 mL) and DCM (200 mL) Acqueous layer was extracted with DCM
- filtrationfiltered
- customto give a residue which
- customwas chromatographed on silica gel (eluant: AcOEt/hexane 3/7)
Sources & evidence
- ORD record
- ord-40b43473ddd047618d55d55b979abc5e
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309253B2
Reaction notes
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