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CAS No. : | 13220-33-2 | MDL No. : | MFCD00003176 |
Formula : | C5H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FLVFPAIGVBQGET-UHFFFAOYSA-N |
M.W : | 101.15 | Pubchem ID : | 93074 |
Synonyms : |
|
Chemical Name : | N-Methyl-3-pyrrolidinol |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H227-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
81% | With dmap; triethylamine; In dichloromethane; at 20℃; for 16h; | (a) 1-Methylpyrrolidin-3-yI methanesulfonate (A 22) 3-Hydroxy-1-methylpyrroldine (0.543 mL, 4.94 mmol) was dissolved in DCM (10 mL)and cooled to 0 C Et3N (0.827 mL, 5.93 mmol), methanesulfonyl chloride (0.421 mL, 5.44 mmol) and DMAP (0.006 g, 0.05 mmol) were added and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with CHCI3 (5 mL) and washed with sat. NaHCO3 (5 mL) and water (2 x 5 mL). The organic layer was concentrated in vacuo to give the title compound A22 as a yellow oil (0.717 g, 81percent yield). 1H NMR (300 MHz, ODd3) O 1.85-2.24 (m, 6H), 2.38- 2.74 (m, 3H), 2.76- 2.91 (m, 3H), 4.95 (m, 1H). |
With triethylamine; In dichloromethane; at -10 - 20℃; for 2.08333h; | A solution of 0.33 cm3 of methanesulfonyl chloride in 7.07 cm3 of dichloromethane is added dropwise to a stirred solution of 0.39 cm3 of <strong>[13220-33-2]1-methyl-3-hydroxypyrrolidine</strong> and 0.62 cm3 of triethylamine in 7.7 cm3 of dichloromethane under a nitrogen atmosphere, at -10° C. The reaction medium is stirred at -10° C. for 5 min and then at a temperature in the region of 20° C. for 2 h, before being concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is taken up with water and ethyl acetate. The solution is stirred for 5 min and is then separated by settling out. The aqueous phase is extracted three times with ethyl acetate. The organic phases are pooled, washed successively with a 5percent aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated under reduced pressure (2.7 kPa) to give 399 mg of methanesulfonic acid (1-methylpyrrolidin-3-yl) ester in the form of a colorless oil. LCMS (electrospray): m/z 180 (MH+), m/z 84 [MH+-(SO2CH3)]. |
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