Tetrahydrofuran → 107259-16-5

HRID 1198611Notes

Reaction equation

HRID 1198611 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[NH2:12][CH:13]([CH:15]1[CH2:19][N:18]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17](=O)[CH2:16]1)[CH3:14].[OH-].[Na+]>O>[NH2:12][CH:13]([CH:15]1[CH2:16][CH2:17][N:18]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:19]1)[CH3:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15223491HCID 15223491, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19000545107259-16-5

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Lithium aluminum hydride (0.55 g, 0.014 mole) was added to tetrahydrofuran (45 mL) with stirring under nitrogen. 4-(1-Aminoethyl)-1-benzyl-2-oxopyrrolidine (1.60 g, 0.0073 mole) was added in several portions over 30 minutes and the reaction was brought to reflux over 75 minutes. The reaction was refluxed 16 hours and cooled to room temperature. The reaction was treated with water (0.55 mL), 10% NaOH (0.55 mL), and water (1.65 mL) slowly dropwise and the solid filtered off and washed with dichloromethane. The combined filtrates were evaporated under reduced pressure to give 3-(1-aminoethyl)-1-benzylpyrrolidine isomer A (1.05 g, 70%) as a yellow oil.

Workup

  1. temperatureto reflux over 75 minutes
  2. temperatureThe reaction was refluxed 16 hours
  3. filtrationthe solid filtered off
  4. washwashed with dichloromethane
  5. customThe combined filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-62c41d28f80d410ca03713b31cb8b067
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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