反応 #657278

反応方程式

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

溶媒

methanol

water

反応条件

後処理

1. 1
   ろ過the reaction mixture was filtered
2. 2
   濃縮concentrated
3. 3
   workup.ADDITIONThe residue was diluted with ethyl acetate
4. 4
   抽出extracted with saturated aqueous sodium carbonate under ice cooling
5. 5
   温度with cooling to pH 5-6 with an aqueous HCl solution
6. 6
   抽出thoroughly extracted with ethyl acetate
7. 7
   洗浄The combined organic layers were washed with brine
8. 8
   乾燥dried over sodium sulfate
9. 9
   濃縮concentrated

実験手順

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.

出典