Molecules 1997, 2, M20

[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diol

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

The reaction and the product ratio shown in the scheme was reported [1]. The two products (2 [1] and 3) were separated by flash chromatography using hexane-ethyl acetate (1:1) as eluent to afford the title compound 3 in the scheme) as a colourless glass (33 mg, 6%).

M.p. 63-64 deg.C.

High Res. MS calc. for C₉H₁₆O₄ M⁺H (CI, NH₃) 189.1128, found: M⁺ 189.1129.

IR (Nujol) cm^-1 3610-3140 (br, s, OH), 1101 (s, C-O).

¹H-NMR (200 MHz, CDCl₃) 1.37 (1H, ddd, J_11ax,11eq 12.7, J_{11ax, 10ax} 12.7 and J_11ax,10eq 4.7 Hz, 11ax-H), 1.49-1.70 (4H, m, 9-CH₂ and 10-CH₂), 1.85-1.98 (3H, m, 11eq-H and 4-CH₂), 2.51 (2H, m, 2 x OH), 3.39 (1H, dd, J_2ax,2eq 10.4 and J_{2ax, 3ax} 10.4 Hz, 2ax-H), 3.61-3.69 (4H, m, 2eq-H, 8-CH₂ and 5-H), 3.94-4.09 (1H, m, 3ax-H).

¹³C-NMR (50 MHz, CDCl₃) 18.3, 24.9, 29.9, 35.6 (CH₂, C-4, C-9, C-10 and C-11), 60.8 (CH₂, C-8), 61.9 (CH, C-3), 64.3 (CH₂, C-2), 71.5 (CH, C-5), 95.7 (quat, C-6).

CI-MS 189 (M⁺H, 8%), 171 (M⁺H-H₂O, 100), 153 (M⁺H-2H₂O, 15), 111 (13), 101 (6).

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, M19.

Sample Availability: Available from Author, 0.1g and from MDPI, MDPI 11866.

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