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CAS No. : | 2133-40-6 | MDL No. : | MFCD00012708 |
Formula : | C6H12ClNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | HQEIPVHJHZTMDP-JEDNCBNOSA-N |
M.W : | 165.62 | Pubchem ID : | 2733200 |
Synonyms : |
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Chemical Name : | H-Pro-OMe.HCl |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate; In water; N,N-dimethyl-formamide; | a (+-)-Methyl N-(3,5-dichlorobenzyl)prolinate To methyl prolinate HCl (0.5 g), K2CO3 (1.25 g) and 3,5-dichlorobenzylchloride (0.59 g) in DMF (5 mL) was added tetrabutylammonium iodide (cat). The solution was stirred overnight, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried (Na2SO4), solvent was removed under reduced pressure, and silica gel flash chromatography (0.5percent methanol/CH2Cl2) yielded the desired product (0.65 g). ES(+) MS m/e=288.3 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With triethylamine; In dichloromethane; | 21 mL of triethylamine was added upon stirring to a solution of 9.23 g of methyl ester of L-proline hydrochloride in 50 mL of methylene chloride. The reaction mixture was stirred during 10 min at 5C, then 7.21 g of <strong>[5555-00-0]2-methyl-3-furoyl chloride</strong> was added upon stirring, and the resulting mixture was stirred during 30 min at 5C and then left overnight. Triethylamine hydrochloride was filtered off, and the filtrate was washed with 10 mL of water and dried over calcium chloride. After removal of the solvent, the residue was dissolved in 10 mL of methylene chloride; the solution was washed with a mixture of 10 mL of concentrated hydrochloric acid and 40 mL of water, then with 30 mL of water, and finally dried over calcium chloride. After removal of the solvent, the residue was kept in a vacuum. Yield 6.5 g (55%), yellow syrup. 1H NMR spectrum (CDCl3), delta, ppm: 1.84-1.95 m (2H, H4-proline), 2.21-2.27 m (2H, H3-proline), 2.40 s (3H, CH3-furan), 3.51-3.67 m (2H, H5-proline), 3.69 s (3H, CH3-proline),4.56 br.t (1H, H2-proline, J 6.6 Hz), 6.4 br.s (1H, H4-furan), 7.19 br.s (1H, H5-furan). 13C NMR spectrum (CDCl3), delta, ppm: 13.31 (C3-furan), 20.27 (C4-proline),25.31 (C3-proline), 48.92 (C5-proline), 53.16 (C2-proline), 53.19 (CH3O), 109.57 (C4-furan), 115.66 (C3-furan), 139.93 (C5-furan), 156.16 (C2-furan), 164.74(CO-amide), 172.80 (CO-ester). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With triethylamine; In dichloromethane; | General procedure: 21 mL of triethylamine was added upon stirring to a solution of 9.23 g of methyl ester of L-proline hydrochloride in 50 mL of methylene chloride. The reaction mixture was stirred during 10 min at 5C, then 7.21 g of <strong>[5555-00-0]2-methyl-3-furoyl chloride</strong> was added upon stirring, and the resulting mixture was stirred during 30 min at 5C and then left overnight. Triethylamine hydrochloride was filtered off, and the filtrate was washed with 10 mL of water and dried over calcium chloride. After removal of the solvent, the residue was dissolved in 10 mL of methylene chloride; the solution was washed with a mixture of 10 mL of concentrated hydrochloric acid and 40 mL of water, then with 30 mL of water, and finally dried over calcium chloride. After removal of the solvent, the residue was kept in a vacuum. |
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