Diethyl Ether → HCID 66661762, compound

HRID 2275614Notes

Reaction equation

HRID 2275614 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 dryed 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. concentrationconcentrated

Sources & evidence

ORD record
ord-6d79bd097dee45aeb348c1f3a4657c06
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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