132883-44-4
(3S)-(-)-3-(Dimethylamino)Pyrrolidine
CAS: 132883-44-4
Molecular Formula: C6H14N2
132883-44-4 - Names and Identifiers
132883-44-4 - Physico-chemical Properties
| Molecular Formula | C6H14N2 |
| Molar Mass | 114.19 |
| Density | 0.899 g/mL at 25 °C (lit.) |
| Boling Point | 160 °C/760 mmHg (lit.) |
| Flash Point | 125°F |
| Vapor Presure | 2.73mmHg at 25°C |
| Specific Gravity | 0.90 |
| pKa | 9.93±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | n20/D 1.4650(lit.) |
| Physical and Chemical Properties | WGK Germany:2 |
132883-44-4 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R10 - Flammable R22 - Harmful if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R38 - Irritating to the skin R37 - Irritating to the respiratory system |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. |
| UN IDs | UN 1993 3/PG 3 |
| WGK Germany | 2 |
| Hazard Class | 3 |
| Packing Group | III |
132883-44-4 - Reference Information
| physical and chemical properties | (3S)-(-)-3-(dimethylamino) pyrrolidine has a colorless to light yellow clear liquid appearance, which is incompatible with strong oxidants. This chemical substance is flammable in the form of liquid and vapor, harmful to swallowing, and can cause skin irritation, cause severe eye irritation and may also cause respiratory irritation. |
| use | (3S)-(-)-3-(dimethylamino) pyrrolidine can be used as a pharmaceutical intermediate for chemical research. |
| application | bafutinib chemical name is N-[3-(4, 5-bipyridyl -2-amino)-4-benzyl]-4-[(3S-(dimethylamino) pyrrolidin-1-methyl]-3-(trifluoromethane) benzamide, It is an effective specific double-AbL-Lyn inhibitor that is found to be more effective than imatinib in the treatment of chronic myeloid leukemia, and its inhibitory effect extends to almost all Bcr-ABL point mutants tested, bafunitinib molecule is mainly composed of pyrimidine ring, benzene ring and (R)-3-dimethylaminopyrrolidine at the end. The nitrogen atom of the terminal dimethylamino group interacts with the carbonyl oxygen atom of the ILe-360 and HIS-361 is combined by hydrogen bonds, which has a significant effect on anti-proliferation activity, in the synthesis of pyrrolidine, the chiral construction of intermediate (R)-3-dimethylaminopyrrolidine (2) and the synthesis of intermediate (S)-1-benzylpyrrolidine (6) are the key to the synthesis. |
| preparation | about the synthesis of (3S)-(-)-3-(dimethylamino) pyrrolidine currently mainly uses L-malic acid as raw material and is synthesized through cyclization, reduction, persulfonylation and deprotection reactions, with a total yield of 31.45%, its structure is directly introduced by using the original hydroxyl group of 3, which avoids the construction of the dimethylamine chiral center. The synthesis process of the intermediate 6(S)-1-benzylpyrrolidine is optimized, and the yield is 90%. (3S)-(-)-3-(dimethylamino) pyrrolidine is synthesized in 87% yields through substitution and reduction, it has important reference significance for the synthesis of this intermediate. The synthesis reaction formula is as follows: Figure 1 (3S)-(-)-3-(dimethylamino) pyrrolidine synthesis reaction formula This synthesis route has the advantages of simple operation, cheap and easy to obtain raw materials, and easy to separate products, which is beneficial to the application and production of the compound. |
Last Update：2024-04-09 15:16:36
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