1-Azabicyclo[2.2.2]octane-4-carbonitrile → Quinuclidin-4-ylmethanamine

HRID 1800815Notes

Reaction equation

HRID 1800815 reaction equation
[C:1]([C:3]12[CH2:10][CH2:9][N:6]([CH2:7][CH2:8]1)[CH2:5][CH2:4]2)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[N:6]12[CH2:9][CH2:10][C:3]([CH2:1][NH2:2])([CH2:8][CH2:7]1)[CH2:4][CH2:5]2

Participants

4

Reactant 2

HCID 1412921-Azabicyclo[2.2.2]octane-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 22056669Quinuclidin-4-ylmethanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of 4-cyanoquinuclidine (0.30 g, 2.2 mmol) in diethyl ether (5 mL) was slowly added to a suspension of LAH (0.167 g, 4.41 mmol) in diethyl ether (15 mL) at 0° C. The reaction was stirred at 23° C. for 3 h, then quenched with sodium sulfate decahydrate and stirred for 30 more minutes. Ethyl acetate was then added and, after 30 minutes, celite was added and the suspension was filtered on celite. The filtrate was concentrated to dryness to give an oil (0.310 g, quant.). The compound was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 1.31-1.40 (6H, m), 2.43 (2H, s), 2.86-2.94 (6H, m).

Workup

  1. customquenched with sodium sulfate decahydrate
  2. stirringstirred for 30 more minutes
  3. additionEthyl acetate was then added and, after 30 minutes
  4. additioncelite was added
  5. filtrationthe suspension was filtered on celite
  6. concentrationThe filtrate was concentrated to dryness
  7. customto give an oil (0.310 g, quant.)
  8. customsuch for the next reaction

Sources & evidence

ORD record
ord-54dffeac107847cb858c202ef847b8b3
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

Loading…