Water → (1-Benzyl-4-methylpyrrolidin-3-YL)methanamine

HRID 1038830Notes

Reaction equation

HRID 1038830 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:18][CH:17]([CH3:19])[CH:16]([C:20]#[N:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCOC(C)=O.O>C1COCC1>[CH2:7]([N:14]1[CH2:18][CH:17]([CH3:19])[CH:16]([CH2:20][NH2:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 41783071-Benzyl-4-methyl-pyrrolidine-3-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 23062042(1-Benzyl-4-methylpyrrolidin-3-YL)methanamineYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of LAH (0.019 g, 0.499 mmol) in THF (5 mL) was added 1-benzyl-4-methylpyrrolidine-3-carbonitrile (0.050 g, 0.250 mmol, Tyger) at about 0° C., then the resulting mixture was stirred at about 25° C. for about 4 h. EtOAc (2 mL) and water (3 mL) were added and the precipitate formed was filtered off. The filtrate was concentrated to give (1-benzyl-4-methylpyrrolidin-3-yl)methanamine (0.05 g, 39%): LCMS (Table 2, Method 1) Rt=0.22 min.; MS m/z: 205 (M+H)+.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f6d3deb04be846babff804ac66ac9ac5
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

Loading…