Reaction #963

ord-355bf43961874334b0dd644d901cbbcf

Reaction equation

[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminium hydride
O
water
[Na+].[OH-]
NaOH
O
water
N#CCC1CCN(Cc2ccccc2)C1
(3RS)-1-benzyl-3-cyanomethyl pyrrolidine
→
NCCC1CCN(Cc2ccccc2)C1
product
Yield 99.0%
NCCC1CCN(Cc2ccccc2)C1
(3RS)-1-benzyl-3-aminoethyl pyrrolidine
Yield 99.0%

Reactants

[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminium hydride
O
water
[Na+].[OH-]
NaOH
O
water
N#CCC1CCN(Cc2ccccc2)C1
(3RS)-1-benzyl-3-cyanomethyl pyrrolidine

Reagents

None

Solvents

CCOCC
diethyl ether
CCOCC
diethyl ether

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added to the mixture
  2. 2
    DryingThe slurry was dried from excess of water with Na2SO4 /cellite
  3. 3
    Filtrationfiltered by suction
  4. 4
    Otherevaporated

Procedure

14.7 g (0.0734 mole) (3RS)-1-benzyl-3-cyanomethyl pyrrolidine dissolved in 220 ml diethyl ether was slowly added to a slurry of 2.94 g of lithium aluminium hydride in 74 ml diethyl ether under an argon atmosphere. The mixture was stirred over night,and 6 ml water, 18 ml 3.75M NaOH-solution and 6 ml water was added to the mixture. The slurry was dried from excess of water with Na2SO4 /cellite, filtered by suction and evaporated to yield 14.84 g (99%) of the product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723444uspto-grants-1998_03