Tetrahydrofuran → HCID 66662607, compound

HRID 557964Notes

Reaction equation

HRID 557964 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.Br[CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18].[Cl-].[NH4+].O1CCCC1>[Zn]>[CH3:18][C:17]([C:2]1([OH:1])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)([CH3:19])[CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 700922-Butene, 1-bromo-3-methyl-HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 66662607HCID 66662607, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a suspension of tert-butyl 3-oxopyrrolidine-1-carboxylate (2.40 g, 0.0130 mol), 4-bromo-2-methyl-2-butene (3.00 mL, 0.0260 mol) in 15.0 mL sat'd. ammonium chloride and tetrahydrofuran (3.00 mL, 0.0370 mol) was added zinc (1.70 g, 0.0260 mol) at rt. Soon after stirring was started, gas and heat were released. After 30 to 45 min., the resulting light grey mixture was filtered through celite. The filtration was extracted with EtOAc. The organic layers were combined, washed with brine, dried (NaSO4) and concentrated in-vacuo. The residue was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to give the desired product. LCMS (M+Na) 278.2.

Workup

  1. temperaturegas and heat
  2. filtrationthe resulting light grey mixture was filtered through celite
  3. filtrationThe filtration
  4. extractionwas extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (NaSO4)
  7. concentrationconcentrated in-vacuo
  8. customThe residue was purified on silica gel
  9. washeluting with 0 to 40% EtOAc in hexane

Sources & evidence

ORD record
ord-6b93ed535f1b40d4ac32a4062a54f12c
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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