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Volume 2003
Issue 3
10.3390/M335
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Short Note

Phenylacetic Acid (3S,6S)-6-Acetoxy-8-methyl-8-aza-bicyclo[3.2.1]oct-3-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), M335; https://doi.org/10.3390/M335
Submission received: 22 February 2003 / Accepted: 22 May 2003 / Published: 1 June 2003
Versions Notes
The fact that the configuration of derivatives of acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl ester was considered having significant influence on the muscarinic activity [1] prompted us to synthesize the chiral compounds with the skeleton in order to study the structure-activity relationship.
Molbank 2003 m335 i001
To a solution of (-)-acetic acid (3S,6S)-3-hydroxy-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl ester [2, 3] (0.22 g, 1.1 mmol) in dichloromethane (2 mL) with pyridine (0.1 mL) was added dropwise phenylacetyl chloride (0.23 mL, 1.7 mmol). The mixture was stirred for 24 h at room temperature. The solution was evaporated in vacuo to dryness. The residue was dissolved in water (5 mL) and basified with concentrated aqueous ammonia. The aqueous solution was extracted with chloroform (5×6 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, evaporated in vacuo, to give phenylacetic acid (3S,6S)-6-acetoxy-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester (0.34 g, 95%) as a pale yellow oil.
[a]D20 = +2.0° (c 1.05, CHCl3).
IR (KBr): 2947, 2858, 1732, 1604.
1H NMR (400 MHz, CDCl3): 1.64-2.15 (m, 6H), 2.03 (s, 3H), 2.44 (s, 3H), 3.08 (s, 1H), 3.21 (m, 1H), 3.61 (s, 2H), 4.95 (m, 1H), 5.21 (dd, J=3.1, 7.6 Hz, 1 H), 7.20-7.36 (m, 5H).
MS: m/z(%) 317 (M+,19.58), 182(38.54), 122(53.49), 94(100), 82(9.95), 43(15.63).
Anal. Calc for C18H23NO4: C 68.14, H 7.26, N 4.42. Found C 67.76, H 7.26, N 4.32.

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. Yang, L. M.; Wang, H. N.; Yan, Z. H. J. Shanghai Second Medical University 1999, 11, 51.
  3. Yan, Z. H.; Lu, Y.; Valler, A.; Liu, H. Z.; Chen, Z. N. Acta Universitatis Medicinalis Secondae Shanghai 2001, 21, 199.
  • Sample Availability: Available from the Authors.

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MDPI and ACS Style

Niu, Y.-Y.; Lu, Y. Phenylacetic Acid (3S,6S)-6-Acetoxy-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl Ester. Molbank 2003, 2003, M335. https://doi.org/10.3390/M335

AMA Style

Niu Y-Y, Lu Y. Phenylacetic Acid (3S,6S)-6-Acetoxy-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl Ester. Molbank. 2003; 2003(3):M335. https://doi.org/10.3390/M335

Chicago/Turabian Style

Niu, Yin-Yao, and Yang Lu. 2003. "Phenylacetic Acid (3S,6S)-6-Acetoxy-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl Ester" Molbank 2003, no. 3: M335. https://doi.org/10.3390/M335

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