Reaction #1100

Reaction equation

4-[O-benzyl-N-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)hydroxylamino]-3-methoxy-2-methylpyridine

→

4-(3,3-Dimethyl-1,5-dioxaspiro[5.5]undec-9-ylamino)-3-methoxy-2-methylpyridine

Solvents

methanol

Conditions

Workup

1. 1
   Otheruntil absorption of hydrogen
2. 2
   FiltrationAfter filtering
3. 3
   Concentrationthe filtrate is concentrated
4. 4
   workup.DISSOLUTIONthe product is dissolved in diisopropyl ether
5. 5
   OtherCrystallization
6. 6
   workup.ADDITIONon addition of hexane

Procedure

6.5 g of 4-[O-benzyl-N-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)hydroxylamino]-3-methoxy-2-methylpyridine in 70 ml of methanol are hydrogenated using 2 g of Raney nickel at normal pressure until absorption of hydrogen is complete. After filtering, the filtrate is concentrated and the product is dissolved in diisopropyl ether. Crystallization takes place on addition of hexane. 4.3 g=90%; m.p.: 45° C.

Source