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Phenylacetic Acid (3S,6S)-6-Acetoxy-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl Ester
 
 
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Volume 2003
Issue 3
10.3390/M336
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Short Note

Acetic Acid 3-(2-Chloro-benzoylamino)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl Ester

by
Yin-Yao Niu
and
Yang Lu
*
Department of Chemistry, Shanghai Second Medical University, Shanghai-200025, People's Republic of China
*
Author to whom correspondence should be addressed.
Molbank 2003, 2003(3), M336; https://doi.org/10.3390/M336
Submission received: 22 February 2003 / Accepted: 22 May 2003 / Published: 1 June 2003
Versions Notes
Acetic acid 3-(2-chloro-benzoylamino)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl ester is a candidate for the study of muscarinic cholinergic agonist and the structure-activity relationship [1].
Molbank 2003 m336 i001
To a solution of acetic acid 3-amino-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl ester [2] (0.214 g, 1.08 mmol) in dichloromethane (1.5 mL) with pyridine (0.1 mL) was added dropwise 2-chlorobenzoyl chloride (0.27 mL, 2.0 mmol). The mixture was stirred for 18 hours at room temperature, then evaporated in vacuo to dryness. The residue was dissolved in water (5 mL) and basified with a saturated aqueous solution of sodium hydrogen carbonate. The aqueous solution was extracted with chloroform (5×4 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, evaporated in vacuo. The resulting residue was chromatographed over silica gel column using CH2Cl2 : CH3OH (20:1 v/v) to give acetic acid 3-(2-chloro-benzoylamino)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl ester (0.29 g, 80%) as a pale yellow oil.
IR (KBr): 3304, 2935, 2856, 1735, 1595.
MS: m/z(%) : 336 (M+, 5.77), 182(3.46), 139(25.44), 122(20.10), 94(100), 82(13.08), 43(7.77).
1H NMR (400 MHz, CDCl3): 1.68 (d, J=15.2 Hz, 1H), 1.90 (d, J=15.9 Hz, 1H), 2.04 (s, 3H), 2.17-2.46 (m, 3H), 2.52 (dd, J=8.6, 14.5 Hz, 1H), 2.55 (s, 3H), 3.25 (s, 1H), 3.42 (m, 1H), 4.20 (dd, J=6.6, 13.1 Hz, 1H), 5.45 (dd, J=3.3, 7.7 Hz, 1H), 6.83 (d, J=5.6 Hz, 1H), 7.27-7.38 (m, 3H), 7.55-7.65 (m, 1H).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgement

The financial support of Shanghai Municipal Educational Committee is acknowledged.

References and Notes

  1. Lu, Y.; Chen, Z. N. Acta Universitatis Medicinalis Secondae Shanghai 1996, 16, 1.
  2. Chu, G. H.; Zhou, Q. T. Acta Pharmaceutica Sinica 1994, 29, 185.
  • Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

Niu, Y.-Y.; Lu, Y. Acetic Acid 3-(2-Chloro-benzoylamino)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl Ester. Molbank 2003, 2003, M336. https://doi.org/10.3390/M336

AMA Style

Niu Y-Y, Lu Y. Acetic Acid 3-(2-Chloro-benzoylamino)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl Ester. Molbank. 2003; 2003(3):M336. https://doi.org/10.3390/M336

Chicago/Turabian Style

Niu, Yin-Yao, and Yang Lu. 2003. "Acetic Acid 3-(2-Chloro-benzoylamino)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl Ester" Molbank 2003, no. 3: M336. https://doi.org/10.3390/M336

APA Style

Niu, Y. -Y., & Lu, Y. (2003). Acetic Acid 3-(2-Chloro-benzoylamino)-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl Ester. Molbank, 2003(3), M336. https://doi.org/10.3390/M336

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