2-Methylene-3-quinuclidone → 2-Methyl-1-azabicyclo[2.2.2]octan-3-ol

HRID 2274852Notes

Reaction equation

HRID 2274852 reaction equation
[CH2:1]=[C:2]1[C:7](=[O:8])[CH:6]2[CH2:9][CH2:10][N:3]1[CH2:4][CH2:5]2>C(O)C.[Pd]>[CH3:1][CH:2]1[CH:7]([OH:8])[CH:6]2[CH2:9][CH2:10][N:3]1[CH2:4][CH2:5]2

Participants

4

Reactant 1

HCID 3229732-Methylene-3-quinuclidone

Product 1

HCID 1071972-Methyl-1-azabicyclo[2.2.2]octan-3-olYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 2-methylenequinuclidin-3-one (3.50 g) in ethanol (30 mL) was reduced over 10% Pd/C (50 wt %) under a H2 atmosphere. When judged complete by TLC (˜3 days), the catalyst was filtered off and the filter cake washed with ethyl acetate. The solvent was removed in vacuo to afford the desired product (2.80 g, 80%) was obtained and used without further purficiation. 1H NMR (400 MHz, CDCl3) 3.37-3.31 (m, 1H), 3.21-3.13 (m, 2H), 3.09-3.00 (m, 1H), 2.97-2.89 (m, 1H), 2.46-2.43 (m, 1H), 2.05-1.91 (m, 4H), 1.34 (d, J=7.6 Hz, 3H) ppm.

Workup

  1. customjudged complete by TLC (˜3 days)
  2. filtrationthe catalyst was filtered off
  3. washthe filter cake washed with ethyl acetate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d30ae1daeaee4436b5ceee1dead57256
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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