Diisopropylamine → HCID 22848795, compound

HRID 257815Notes

Reaction equation

HRID 257815 reaction equation
C(NC(C)C)(C)C.[CH2:8]([C@@H:10]1[C@@H:14]([CH2:15][C:16]2[N:20]([CH3:21])[CH:19]=[N:18][CH:17]=2)[CH2:13][NH:12][C:11]1=[O:22])[CH3:9].C([C:25]([O:27][CH3:28])=[O:26])#N>O1CCCC1.CCCCCC>[C:25]([N:12]1[CH2:13][C@H:14]([CH2:15][C:16]2[N:20]([CH3:21])[CH:19]=[N:18][CH:17]=2)[C@@H:10]([CH2:8][CH3:9])[C:11]1=[O:22])([O:27][CH3:28])=[O:26]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 28660Carbonocyanidic acid, methyl esterHCID 15021363HCID 15021363, compound

Product 1

HCID 22848795HCID 22848795, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a solution of diisopropylamine (58 mg, 0.57 mmol) in tetrahydrofuran (THF) (2 mL) at 0° was added 251 μL of a 2.5 M solution of D-butyl lithium (0.63 mmol) in hexane. The solution was stirred at 0° for 15 min., then cooled to -78° and (3R, 4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl) methyl]-2-pyrrolidinone (118.2 mg, 0.57 mmol) in THF (2.5 mL) was added via cannula, followed by a THF (0.5 mL) rinse. After 2 hours at -78 , methyl cyanoformate (50.9 mg, 0.60 mmol) was added and the reaction was maintained at -78° for 1.5 hours, then warmed to room temperature for 15 hours. The reaction was quenched with saturated aqueous NaHCO3, extracted three times with CHCl3, dried (Na2SO4), filtered, concentrated and the residue was chromatographed on silica gel (5% MeOH satured with NH3 /CHCl3) to give 44.3 mg of (3R, 4R)-1-carbomethoxy-3-ethyl-4[(1-methyl-1H-imidazol-5-yl)methyl]-2-pyrrolidinone as an oil (28%).

Workup

  1. temperaturecooled to -78°
  2. washrinse
  3. temperaturethe reaction was maintained at -78° for 1.5 hours
  4. customThe reaction was quenched with saturated aqueous NaHCO3
  5. extractionextracted three times with CHCl3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was chromatographed on silica gel (5% MeOH satured with NH3 /CHCl3)

Sources & evidence

ORD record
ord-8023c8fb54684e5fb78e77fd102d6a93
Source dataset
uspto-grants-1993_11
Patent number
US05264449

Reaction notes

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