Molecules 1997, 2, M22
Margaret A. Brimble* and Andrew D. Johnston
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia. phone +61-2-9351-2750, fax +61-2-9351-6650, e-mail [email protected], http://www.chem.usyd.edu.au/~brimble
Received: 18 June 1997 / Published: 20 June 1997
To a solution of [3S*,5S*,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (1) [1] (33 mg, 0.17 mmol) in dichloromethane (10 ml) was added triethylamine (54 mg, 0.53 mmol), acetic anhydride (34 mg, 0.34 mmol) and 4-dimethylaminopyridine (3 mg). The reaction mixture allowed to stand at room temperature for 1 h, then quenched with water (2.0 ml), extracted with dichloromethane (2x 50 ml) and dried over sodium sulphate. Removal of the solvent under reduced pressure gave a pale yellow oil, that was purified by flash chromatography using hexane-ethyl acetate (2:1) as eluent to afford [3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undec-3,5-diyl diacetate (2) (43 mg, 90%) as a colourless oil.
High Res. MS calc. for C13H20O6 M+H (CI, NH3) 273.1329, found: M+ 273.1338.
IR (Nujol) cm-1 1720 [s, C=O (ester)], 1010 (s, C-O).
1H-NMR (200 MHz, CDCl3) 1.34 (1H, ddd, J11ax,11ex 14.0, J11ax,10ax 14.0 and J11ax,10eq 5.2 Hz, 11ax-H), 1.49-1.77 (6H, m, 4-CH2, 9-CH2 and 10-CH2), 2.01 (3H, s, Ac), 2.09 (3H, s, Ac), 1.99-2.11 (1H, m, 11eq-H), 3.48 (1H, dd, J2ax,2eq10.5 and J2ax, 3ax 10.5 Hz, 2ax-H), 3.62-3.80 (3H, m, 8-CH2 and 2eq-H), 4.87 (1H, t, J5,4 3.1 Hz, 5-H), 4.95-5.11 (1H, m, 3-H).
13C-NMR (50 MHz, CDCl3) 18.1, 24.7, 29.9, 30.2 (CH2, C-4, C-9, C-10 and C-11), 21.1 (CH3, Ac), 60.7, (CH2, C-2), 60.8 (CH, C-3), 64.5 (CH2, C-2), 72.1 (CH, C-5), 96.1 (quat, C-6), 170.0, 171.2 (quat, 2 x C=O).
CI-MS 273 (M+H, 12%), 213 (100), 153 (72), 135 (8).
Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.
References
1.Brimble, M. A.; Johnston, A. D. Molecules 1997, 2, M20.
Sample Availability: No sample available.
© 1997 MDPI. All rights reserved.