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Short Note

[4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undecane-4,5-diol

by
Margaret A Brimble
* and
Andrew D Johnston
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(6), M19; https://doi.org/10.3390/M19
Submission received: 18 June 1997 / Published: 20 June 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 02 m19 i001
A solution of [3R*,4R*,5S*,6S*]-3,4-epoxy-1,7-dioxaspiro[5.5]undecan-5-ol (1) (561 mg, 3.01mmol) in dry tetrahydrofuran (30 ml) under a nitrogen atmosphere was cooled to 0 deg.C in an ice/water bath. Lithium aluminium hydride (4.52 ml, of a 1 mol L-1 solution in THF, 4.52 mmol) was added in 3 portions over 1 minute, and the reaction mixture allowed to stir at 0 deg.C for 1 h then room temperature for 12 h. After quenching with sodium dihydrogen phosphate solution (10 ml, 10% w/v), the reaction mixture was extracted with ethyl acetate (3x 50 ml), the combined extracts washed with water (10 ml) and dried over sodium sulphate. Removal of the solvent under reduced pressure gave a colourless oil, which was purified by flash chromatography using hexane-ethyl acetate (2:1) as eluent to afford [4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undecane-4,5-diol (2) (310 mg, 55%) as colourless needles [1].
M.p. 135-137 deg.C.
IR (Nujol) cm-1 3600-3150 (br, s, OH), 1082 (s, C-O).
1H-NMR (400 MHz, CDCl3) 1.47 (1H, ddd, J11ax,11eq 13.3, J11ax,10ax 13.3 and J11ax,10eq 4.4 Hz, 11ax-H), 1.54-1.81 (5H, m, 9-CH2, 10-CH2 and 3ax-H), 1.90 (1H, dt, J11eq,11ax 13.3 and J11eq,10 2.6 Hz, 11eq-H), 2.05-2.14 (1H, m, 3eq-H), 3.41 (1H, dd, J5,4 7.4 and J5,OH 3.7 Hz, 5-H), 3.62 (1H, ddd, J2eq, 2ax 11.8, J2eq,3ax 5.5 and J2eq,3eq 2.3 Hz, 2eq-H), 3.71-3.99 (6H, m, 8-CH2, 4-H, 2ax-H, 4-OH and 5-OH).
13C-NMR (100 MHz, CDCl3) 17.6, 24.8, 27.6, 30.6 (CH2, C-3, C-9, C-10 and C-11), 55.6 (CH2, C-2), 61.3 (CH2, C-8), 68.6 (CH, C-4), 71.1 (CH, C-5), 98.4 (quat, C-6).
CI-MS 189 (M+H, 85%), 171 (M+H-H2O, 100), 153 (10), 118 (13), 115 (8), 101 (80), 83 (10).
Anal. calc. for C9H16O4 C, 57.44; H, 8.57%; M+H, 189.1127, found C, 57.50; H, 8.42%; M+H (CI, NH3), 189.1134.

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgment: 

The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

References and Notes

  1. Another product (3 in the Scheme, a colourless glass, 33mg, 6%) will be reported in the following short note. Brimble, M. A.; Johnston, A. D. Molecules 1997, 2, M20.
  • Sample Availability: No sample available.

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MDPI and ACS Style

Brimble, M.A.; Johnston, A.D. [4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undecane-4,5-diol. Molecules 1997, 2, M19. https://doi.org/10.3390/M19

AMA Style

Brimble MA, Johnston AD. [4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undecane-4,5-diol. Molecules. 1997; 2(6):M19. https://doi.org/10.3390/M19

Chicago/Turabian Style

Brimble, Margaret A, and Andrew D Johnston. 1997. "[4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undecane-4,5-diol" Molecules 2, no. 6: M19. https://doi.org/10.3390/M19

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