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

Molbank 2003, M336

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

Yin-Yao Niu and Yang Lu*

Department of Chemistry, Shanghai Second Medical University, Shanghai-200025, People's Republic of China

Tel. +86 21 63846590-776464, Fax. +86 21 53065329, E-mail: [email protected] and [email protected]

Received: 22 February 2003 / Accepted 22 May 2003 / Published 1 June 2003

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].

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).

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.