2-Butene, 1-bromo-3-methyl- → HCID 18922258, compound

HRID 2396787Notes

Reaction equation

HRID 2396787 reaction equation
[Li+].CC([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:22])[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:14].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>C1COCC1>[CH3:9][O:10][C:11](=[O:22])[CH:12]([CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH3:14]

Participants

5

Reactant 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 2724682Lithium diisopropylamideHCID 14018930Methyl N-(tert-butoxycarbonyl)-N-methylglycinate

Product 1

HCID 18922258HCID 18922258, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2 M solution of LDA (70.32 ml, 0.14 mol) was added (via syringe) to a solution of N-t-butoxycarbonyl-sarcosine methyl ester (26 g, 0. 1279 tool) in 40 ml of dry THF at -78° C. under nitrogen and the mixture was stirred at this temperature for 30 minutes. To the above mixture was added 4 -bromo-2-methyl-2-butene (20 g, 0.134 mol) with stirring continuing at -78° C., and the resulting mixture was allowed to warm to room temperature. The reaction mixture was quenched with a saturated ammonium chloride solution at -78° C, and then water was added, and the resulting reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo to yield a yellow oil, which was purified by silica gel column chromatography (20% ethyl acetate in hexane) to afford 22.1 g (63.7 %) of N-t-butoxycarbonyl-2-(3-methyl-2-butenyl) sarcosine methyl ester as an oil.

Workup

  1. stirringwith stirring
  2. customcontinuing at -78° C.
  3. customThe reaction mixture was quenched with a saturated ammonium chloride solution at -78° C
  4. additionwater was added
  5. customthe resulting reaction mixture
  6. extractionwas extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto yield a yellow oil, which
  11. customwas purified by silica gel column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0e411d8e6fe54150a26d9635fa417368
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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