Diethyl Ether → HCID 66661762, compound

HRID 557899Notes

Reaction equation

HRID 557899 reaction equation
C([Li])CCC.Cl.Br[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.CCOCC.[O:19]=[C:20]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]1>CCCCCC>[OH:19][C:20]1([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 881004-Bromopyridinium chlorideHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 66661762HCID 66661762, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

1.600 M of n-Butyllithium in hexane (0.810 mL) was added to a solution of 4-bromopyridine hydrochloride (210 mg, 1.1 mmol) in ether (5 mL, 0.05 mol) at −78° C. The solution was stirred at −78° C. for 30 min. and then tert-butyl 3-oxopyrrolidine-1-carboxylate (200 mg, 0.001 mol) was added and the temperature was maintained at −78° C. for 3 hours. The reaction mixture was quenched with water, extracted with AcOEt. The organic layer was dried with MgSO4, and concentrated to afford the desired product.

Workup

  1. temperaturethe temperature was maintained at −78° C. for 3 hours
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer was dried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0a599727686a4a7f9b7b2fcc39a87d2a
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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