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

HRID 1004

Reaction equation

HRID 1004 reaction equation
C(O[N:9]([C:23]1[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[C:24]=1[O:30][CH3:31])[CH:10]1[CH2:22][CH2:21][C:13]2([O:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][O:14]2)[CH2:12][CH2:11]1)C1C=CC=CC=1>CO.[Ni]>[CH3:19][C:16]1([CH3:20])[CH2:17][O:18][C:13]2([CH2:12][CH2:11][CH:10]([NH:9][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[C:24]=3[O:30][CH3:31])[CH2:22][CH2:21]2)[O:14][CH2:15]1

Participants

4

Reactant 1

HCID 196939824-[O-Benzyl-N-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)hydroxylamino]-3-methoxy-2-methylpyridine

Product 1

HCID 196939904-(3,3-Dimethyl-1,5-dioxaspiro[5.5]undec-9-ylamino)-3-methoxy-2-methylpyridine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

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.

Workup

  1. customuntil absorption of hydrogen
  2. filtrationAfter filtering
  3. concentrationthe filtrate is concentrated
  4. dissolutionthe product is dissolved in diisopropyl ether
  5. customCrystallization
  6. additionon addition of hexane

Sources & evidence

ORD record
ord-f4dba46589654bd6a818f29b87cc4306
Source dataset
uspto-grants-1998_03
Patent number
US05723450

Linked notes

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