1508261-86-6
(S)-2-methylpyrrolidine-2-carboxylic acid (Hydrochloride)
CAS: 1508261-86-6
Molecular Formula: C6H12ClNO2
1508261-86-6 - Names and Identifiers
1508261-86-6 - Physico-chemical Properties
| Molecular Formula | C6H12ClNO2 |
| Molar Mass | 165.61798 |
| Storage Condition | Inert atmosphere,Room Temperature |
| Use | This product is for scientific research only and shall not be used for other purposes. |
1508261-86-6 - Reference Information
| Application | (S)-2-methylproline hydrochloride is an amino acid derivative-Proline is obtained by three-step preparation, is an organic synthesis intermediate and pharmaceutical intermediate, can be used in laboratory research and development process and biochemical research and development process. |
| preparation method | Step 1: Synthesis of intermediate 2 to (S)-proline (11.4g,99mmol) mgSO4 (30g) was added to a suspension of Chloral Hydrate (35g,211.6mmol) in MeCN (ml). The mixture was heated at 60 °c for 24 hours, then stirred at room temperature for 2 days and then filtered. The residue was washed with EtOAc and the combined organic phases were concentrated. The residue was dissolved in EtOAc and the resulting solution was washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated. The crude was recrystallized from EtOH to give oxazolidinone 2(10.2g,40%) as a white solid. Synthesis of intermediate 3 an ice-cold solution of 2m LDA(2.6mL,5.20mmol) was added dropwise to oxazolidinone 2(1.05g,4.30mmol) at -78 °c. Of THF(30ml) in solution. After 30 minutes, MeI(0.54mL,8.67mmol) was added dropwise and the mixture was warmed to -30 °c over 2 hours. Water was added before the mixture was warmed to RT. The mixture was extracted with CHCl3 and the combined extracts were washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (0 to 100% EtOAc in petroleum ether) to give oxazolidinone 3(430mg,39%) as a light yellow oil. Step 3, synthesis of (S)-2-methylproline hydrochloride (4) oxazolidinone 3(430mg,1.66mmol) was added to 6m HCl(5ml), and heated to reflux for 3 hours. The mixture was concentrated and the residue was triturated with hot acetone. After cooling and standing (24 h), the acetone was decanted and the residue was dried, leaving the HCl salt as a white solid (160mg). 1H NMR (3.36 MHz,D2O) 3.47-2.43 (m,1H), 2.35-2.17 (m,1H), 1.94-1.64 (m,3H), (s,3H). Crude 4 was dissolved in MeOH and passed through an amberlysta 21 resin column (eluted with water) to give a zwitterionic form as a white solid (81mg,38%). |
Last Update：2024-04-09 20:52:54
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