Sodium Hydroxide → HCID 66936044, compound

HRID 1366531Notes

Reaction equation

HRID 1366531 reaction equation
CO/[N:3]=[C:4]1/[C:5]([CH3:18])([CH3:17])[N:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH2:7][CH2:8]/1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH3:17][C:5]1([CH3:18])[CH:4]([NH2:3])[CH2:8][CH2:7][N:6]1[CH2:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 87210078HCID 87210078, compound

Product 1

HCID 66936044HCID 66936044, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (3E)-2,2-dimethyl-1-(phenylcarbonyl)-3-pyrrolidinone O-methyloxime (1.9492 g, 7.914 mmol) in THF (80 mL) was added lithium aluminum hydride (0.900 g, 23.72 mmol), and the mixture was heated at 65° C. and stirred for 5 h. The mixture was cooled to 0° C., and Na2SO4.10H2O (2 g) was added. The mixture was stirred for 30 min, and 1 N aq. NaOH (100 mL) was then added. The mixture was extracted with Et2O (3×150 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude racemic 2,2-dimethyl-1-(phenylmethyl)-3-pyrrolidinamine (1.8247 g, >100% crude yield) as a light yellow oil. LCMS: (M+H)+: 205.2.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred for 30 min
  3. extractionThe mixture was extracted with Et2O (3×150 mL)
  4. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-770b5be7e9c8469a9f710275435d62a3
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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