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Chemical Structure| 13118-11-1 Chemical Structure| 13118-11-1

Structure of 13118-11-1

Chemical Structure| 13118-11-1

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Product Details of [ 13118-11-1 ]

CAS No. :13118-11-1
Formula : C18H25NO3
M.W : 303.40
SMILES Code : O=C(OC1CN(C)CC1)C(O)(C2CCCC2)C3=CC=CC=C3
MDL No. :MFCD12911798

Safety of [ 13118-11-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P330-P501

Application In Synthesis of [ 13118-11-1 ]

* 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.

  • Downstream synthetic route of [ 13118-11-1 ]

[ 13118-11-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 13220-33-2 ]
  • [ 19833-96-6 ]
  • [ 13118-11-1 ]
YieldReaction ConditionsOperation in experiment
72% With sodium; In n-heptane; for 3h; A solution of 2 (2.20 g, 9.4 mmol) and N-methyl-3-pyrrolidinol (3, 1.30 g, 13 mmol) in 40 ml of n-heptane was heated until 20 ml of heptane had been distilled. About 0.003 g of sodium was added, and the solution was stirred and heated for 2 h as the distillation was continued. More heptane was added at such a rate as to keep the reaction volume constant. Additional sodium was added at the end of an hour. The solution was then cooled and extracted with 3N HCl. The acid extract was made alkaline with concentrated NaOH and extracted three times with ether. Removal of the dried ether solution gave a crude oil. Flash chromatography of the crude product on silica gel with 8:1 EtOAc:EtOH gave pure product 4 (2.053 g, 72percent). Analysis for C18H25NO3. Calcd: C, 71.26; H, 8.31; N, 4.62. Found: C, 71.55; H, 8.44; N, 4.68. 1H NMR(CDCl3, 500 MHz): 1.27-1.35, 1.40-1.47, 1.54-1.60, 1.75-1.90 [8H, m, (CH2)4], 2.12-2.30, 2.52-2.57, 2.64-2.81 (6H, m CH2NCH2CH2), 2.33, 2.36 (3H, 2s, NCH3), 2.93 [(1H, p, CHC(OH)], 3.83 (1H, bs, OH), 5.23 (1H, m, CO2CH), 7.23-7.36, 7.64-7.67 (5H, m, Ph) ppm.
  • 2
  • [ 13220-33-2 ]
  • [ 427-49-6 ]
  • [ 13118-11-1 ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 13220-33-2 ]
  • [ 427-49-6 ]
  • [ 530-62-1 ]
  • [ 13118-11-1 ]
  • [ 1404453-84-4 ]
  • 4
  • [ 13220-33-2 ]
  • cyclopentylmandelic acid [ No CAS ]
  • [ 13118-11-1 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole; In toluene; for 5h;Heating; Step 1: Preparation of Glycopyrrolate Base (Mixture of Erythro/Threo Base) Cyclopentylmandelic acid is activated by reaction under heating with 1,1-carbonyldiimidazole in toluene. N-methyl-3-pyridinol is added and stirred for at least five hours. After in-process testing to confirm completion of reaction, the mixture is cooled, washed with water, and the toluene solution concentrated to a mixture containing between 20-40percent toluene and less than 4percent residual cyclopentyl mandelic acid. This mixture is used directly in the next step.
 

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