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CAS No. : | 204387-53-1 | MDL No. : | MFCD06656005 |
Formula : | C5H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 96.13 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 8,6.1 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P361-P363-P403+P233-P405-P501 | UN#: | 2922 |
Hazard Statements: | H302-H315-H318-H311+H331 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | () 3- (1,5-di-(2-(S)-Cyanopyrrolidin-1-yl)pentane-1, 5-dione carbamic acid tert-but ester 3-tert-Butoxycarbonylaminopentanedioic acid (0.10 g, 0.4 MMOL) was dissolved in DCM (9 ml) and DMF (1 ML). HOAT (0.11 G, 0.81 MMOL) and then EDAC (0.16 g, 0.81 MMOL) were added at 0C, and the reaction mixture was stirred for/2 hour at 0C. Pyrrolidine-2- (S)- carbonitrile (0.17 g, 0.81 MMOL) and DIEA (0.21 ml, 1.21 MMOL) were added and the mixture was slowly heated to room temperature, and stirred for 3 days. The reaction mixture was evaporated and dissolved in ethyl acetate (50 ml) and water 50 (ML). 1 M Potassium hydrogen sulphate (30 ML) was added until pH=2. The organic layer was isolated, and washed with water (10 ml), aqueous sodium hydrogen carbonate (10 ML), and brine (10 ml), and then dried over sodium sulphate, filtered and evaporated, and purified on preparative HPLC (Method A) to afford 85 mg (53%) of () 3- (1, 5-DI- (2- (S)-CYANOPYRROLIDIN-1-YL) PENTANE)-1, 5- dione carbamic acid ter-butyl ester as white crystals. HPLC-MS: (method B): m/z: 304 (M+1-Boc). Preparative HPLC (Method A): Rt= 9.08 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With methanesulfonic acid; In dichloromethane; for 2h;Reflux; | In 120 mL of dichloromethane, 8.93 g (45.5 mmol) of (S)-N-Boc-2-cyano-pyrrolidine, 5.77 g (60 mmol) of methanesulfonic acid were added, and the mixture was heated to reflux for 2 hours. The temperature was lowered to room temperature, distilled water was added, liquid separation, and the organic phase was concentrated, and (S)-2-cyano-pyrrolidine 4.23 g (44 mmol) was obtained by column chromatography.The yield was 97%. |
With methanesulfonic acid; at 40 - 45℃; | Dichloromethane (500 ml), L-Prolinamide (100 g), potassium carbonate (60.50 g) were mixed and stirred under nitrogen atmosphere in round bottom flask The reaction mass was cooled to 10-15C and then Di-tert-butyl dicarbonate (210.30 g) was added. Reaction mixture was stirred till completion of the reaction. After completion water (500m1) was added and product was extracted in dichloromethane. Dichloro methane was removed and then dimethyl formamide (140 ml) and dichloromethane (700 ml) were added under nitrogen atmosphere. Cyanuric chloride (72.70 g) was charged in 2-3 equal lots to the reaction mass at 20-25C under nitrogen atmosphere. The reaction mass was maintained at 35-40C for 4-5 hrs. After completion of the reaction solid was filtered and washed with MDC. Methane sulfonic acid (252.60 g) was added to the filtrate and heated the reaction mass to 40-45C for 3-4 hrs. After completion of the reaction the reaction mass was cooled at 0-5C and Triethyl amine (88.65 g) and Chloroacetyl chloride (118.70 g) were added. The reaction mass was maintained at 20-30C for 1-2 hrs under nitrogen atmosphere. After completion of the reaction water was charged and product was extracted in dichloromethane. Organic layer was washed first with dilute HC1 solution and then with ammonia solution. Organic solvent was removed and product was crystallized using isopropyl alcohol. Yield: 75.0gm |