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CAS No. : | 427-49-6 | MDL No. : | MFCD00019296 |
Formula : | C13H16O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WFLUEQCOAQCQLP-UHFFFAOYSA-N |
M.W : | 220.26 | Pubchem ID : | 98283 |
Synonyms : |
|
Signal Word: | Danger | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H318-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 |
---|---|---|
Example 1; Preparation of (3S,2'R)- and (3R,2'S)-3-[(cyclopentyl-hydroxyphenylacetyl)-oxy]-l,l- dimethylpyrrolidinium bromide; 30 g of cyclopentyl mandelic acid, dissolved in 135 g dimethylformamide (DMF), were treated with 27 g carbonyldiimidazole at 180C (in portions) to form the "active amide". After the addition of 16.9 g of l-methyl-pyrrolidin-3-ol, the mixture was heated to 600C within 1 hour and stirred for 18 hours at this temperature. After checking for complete conversion, the mixture was cooled and 200 g water was added. The mixture was extracted with 200 g toluene and the extract was washed with water three times. The organic phase was concentrated to obtain cyclopentyl-hydroxy-phenyl-acetic acid l-methyl-pyrrolidin-3-yl ester as an about 50percent solution in toluene, ready to use for the next step.This solution was diluted with 120 g of n-propanol and cooled to O0C. 16.8 g methyl bromide was introduced and the mixture was stirred for 2 hours and then gradually heated to 60°C to evaporate the excess methyl bromide into a scrubber. The mixture was then cooled to 500C and seed crystals were added to facilitate crystallisation. The temperature was then slowly reduced over 18 hours to 15°C. The solid was then isolated by filtration to obtain 22.7 g after drying. It was composed mainly of one pair of enantiomers, a racemic mixture of (3S,2'R)- and (3R,2'S)-3-[(cyclopentyl-hydroxyphenylacetyl)-oxy]-l,l- dimethylpyrrolidinium bromide, with a purity greater than 90percent (by HPLC). The other pair of diastereoisomers ((3R,2'R)- and (3S,2'S)-3-[(cyclopentyl-hydroxyphenyl-acetyl)-oxy]-l,l- dimethylpyrrolidinium bromide) remains mainly in the filtrate as those compounds are significantly more soluble in n-propanol than the other stereoisomers.The solid obtained is further recrystallised in n-propanol (1:10 wt) to give pure (3S,2'R)- and (3R,2'S)-3-[(cyclopentyl-hydroxyphenylacetyl)-oxy]-l,l-dimethylpyrrolidinium bromide i.e. purity >; 99.9percent as determined by high performance liquid chromatography (HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1 : Synthesis of 2-Cyclopentyl-2-hydroxy-lambda/-[2-(lH-imidazol-l-yl)ethyll-2- phenylacetamide (Compound No. 1) <n="36"/>To a solution of the hydrochloride salt of 2-(lH-imidazol-l-yl)ethanamine (0.5 g, 4.50 mmol) in chloroform (10 ml) was added N-methyl morpholine (2.96 ml, 27.02 mmol) and stirred the mixture for 5 to 10 minutes at the room temperature followed by the addition of 2- cyclopentyl-2-hydroxy-2-phenyl acetic acid (0.99 g, 4.5 mmol) and hydroxy benzotriazole (0.60 g, 4.5 mmol) at room temperature. The resulting reaction mixture was stirred for 30-45 minutes followed by the addition of l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and again stirred for over night. The mixture was diluted with water and stirred for 10-15 minutes followed by the addition of dichloromethane. The mixture was stirred for 15-20 minutes. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by preparative column chromatography using 10 % methanol in dichloromethane as eluent to furnish the title compound. Yield: 70 mg.1H NMR (CDCl3)delta: 7.60-7.31 (5H, m), 6.99 (IH, s), 6.99 (IH, s), 6.65 (IH, s), 4.01-4.00 (2H, m), 3.99-3.49 (2H, m), 3.11-3.07 (IH, m), 1.64-1.42 (8H, m). |
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