3-(1H-indol-3-yl)-1-methylpyrrolidine-2,5-dione → 3-(1-Methylpyrrolidin-3-yl)-1H-indole

HRID 1884828Notes

Reaction equation

HRID 1884828 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:14][C:13](=O)[N:12]([CH3:16])[C:11]2=O)=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:16][N:12]1[CH2:13][CH2:14][CH:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 153262663-(1H-indol-3-yl)-1-methylpyrrolidine-2,5-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 193373-(1-Methylpyrrolidin-3-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3-(1-H-indol-3-yl)-1-methyl-pyrrolidine-2,5-dione (1.4 g) in tetrahydrofuran is treated with LiAlH4 (12 mL, 1.0 M solution, 2 equiv), stirred at 50° C. for 8 hr, cooled to room temperature, quenched with water and 15% aqueous NaOH and filtered. The filtrate is dried over MgSO4 and concentrated in vacuo to afford the title product as an oil, 1.1 g, identified by HPLC and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water and 15% aqueous NaOH
  3. filtrationfiltered
  4. dry with materialThe filtrate is dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a2794bcac5843f5bd95dc9e5f502dff
Source dataset
uspto-grants-2004_07
Patent number
US06767912B2

Reaction notes

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