Reaction #1056994

Reaction equation

8-methyl-8-aza-bicyclo[3.2.1]octan-3-one oxime

acetic acid

→

8-methyl-8-azabicyclo[3.2.1]oct-3-ylamine

Yield 100.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherA 500-mL Parr hydrogenation vessel was purged with nitrogen
2. 2
   OtherThe bottle was evacuated
3. 3
   workup.ADDITIONcharged with hydrogen gas to a pressure of 50 psi
4. 4
   OtherThe hydrogen was then evacuated
5. 5
   workup.ADDITIONnitrogen charged to the bottle
6. 6
   workup.ADDITIONThe reaction mixture was then mixed with Celite 521 (5.0 g)
7. 7
   Filtrationfiltered
8. 8
   Otherthe filtrate evaporated to a solid residue
9. 9
   workup.DISSOLUTIONThis residue was dissolved in methanol (100 mL)
10. 10
    workup.ADDITIONthis solution treated with sodium carbonate (10 g)
11. 11
    workup.ADDITIONThe resulting suspension was added diethyl ether (50 mL)
12. 12
    Filtrationfiltered
13. 13
    OtherEvaporation of the filtrate to dryness

Procedure

A 500-mL Parr hydrogenation vessel was purged with nitrogen and charged with platinum (IV) oxide (1.28 g, 5.64 mmol), 8-methyl-8-aza-bicyclo[3.2.1]octan-3-one oxime (4.00 g, 26.0 mmol), acetic acid (11 mL) and ethanol (110 mL). The bottle was evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 24 h on a Parr hydrogenation apparatus. The hydrogen was then evacuated and nitrogen charged to the bottle. The reaction mixture was then mixed with Celite 521 (5.0 g), filtered, and the filtrate evaporated to a solid residue. This residue was dissolved in methanol (100 mL) and this solution treated with sodium carbonate (10 g). The resulting suspension was added diethyl ether (50 mL) and filtered. Evaporation of the filtrate to dryness afforded 3.64 g (100%) of 8-methyl-8-azabicyclo[3.2.1]oct-3-ylamine as a white solid: 1H NMR (300 MHz, CD3OD) δ 5.18 (br s, 2H), 3.35 (br s, 2H), 3.21 (t, J=6.6 Hz, 1H), 2.40 (s, 3H), 2.26-2.00 (m, 6H), 1.68-1.58 (m, 2H).

Source