反应 #543594

反应方程式

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

3-(3,4-dimethoxybenzoyl)propionic acid

dihydrochloride

(S)-octahydro-pyrrolo[1,2-a]pyrazine

ethyldiisopropylamine

→

title compound

1-(3,4-Dimethoxyphenyl)-4-((S)-hexahydropyrrolo[1,2-a]pyrazin-2-yl)butane-1,4-dione

溶剂

dichloromethane

N,N-dimethylformamide

N,N-dimethylformamide

ethyl acetate

反应条件

后处理

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 16 hours, while it
2. 2
   温度was warming up to room temperature
3. 3
   洗涤washed with a saturated aqueous solution of sodium hydrogen carbonate
4. 4
   萃取The aqueous phase was extracted with ethyl acetate (2×100 ml)
5. 5
   干燥The combined organic layers were dried over magnesium sulphate
6. 6
   其他The solvent was removed in vacuo
7. 7
   其他The crude product was purified by HPLC on a C18-reversed phase column
8. 8
   workup.ADDITIONa mixture of 1% trifluoroacetic acid in water and acetonitrile as eluent

实验过程

At 0° C., 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (479 mg, 2.5 mmol) was added to a solution of 3-(3,4-dimethoxybenzoyl)propionic acid (596 mg, 2.5 mmol) and 3-hydroxy-3H-dihydrobenzo[d][1,2,3]triazin-4-one (408 mg, 2.5 mmol) in a mixture of dichloromethane (10 ml) and N,N-dimethylformamide (10 ml). The reaction mixture was stirred for 25 min at 0° C. A solution of the crude dihydrochloride salt of (S)-octahydro-pyrrolo[1,2-a]pyrazine in N,N-dimethylformamide (4 ml) and ethyldiisopropylamine (3.0 ml, 17.5 mmol) were added successively. The reaction mixture was stirred for 16 hours, while it was warming up to room temperature. It was diluted with ethyl acetate (200 ml) and washed with a saturated aqueous solution of sodium hydrogen carbonate. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by HPLC on a C18-reversed phase column, using a mixture of 1% trifluoroacetic acid in water and acetonitrile as eluent, to give 148 mg of the title compound.

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