Реакция #657278

Уравнение реакции

4-benzyloxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

→

4-hydroxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

Растворители

methanol

water

Условия реакции

Обработка

1. 1
   Фильтрацияthe reaction mixture was filtered
2. 2
   Концентрированиеconcentrated
3. 3
   workup.ADDITIONThe residue was diluted with ethyl acetate
4. 4
   Экстракцияextracted with saturated aqueous sodium carbonate under ice cooling
5. 5
   Температураwith cooling to pH 5-6 with an aqueous HCl solution
6. 6
   Экстракцияthoroughly extracted with ethyl acetate
7. 7
   ПромывкаThe combined organic layers were washed with brine
8. 8
   Сушкаdried over sodium sulfate
9. 9
   Концентрированиеconcentrated

Методика

To a solution of 4-benzyloxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (22.6 g, 53.7 mmol) in methanol (226 ml) and water (22.6 ml) in a Parr shaker type hydrogenator was added 5% Pd/C (22.6 g). After hydrogenation under 4 bars H2 at 36° C. for 22 hours, the reaction mixture was filtered and concentrated. The residue was diluted with ethyl acetate and extracted with saturated aqueous sodium carbonate under ice cooling. The organic layer was discarded, the aqueous alkaline phase acidified with cooling to pH 5-6 with an aqueous HCl solution and thoroughly extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. Yield: 13.0 g of 4-hydroxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2.2) as a solid, mp 239-241° C.

Источник