[3R*,5S*,6S*]-5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-yl 3,5-Dinitrobenzoate

Margaret A. Brimble; Andrew D. Johnston

doi:10.3390/M17

and

Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia

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Author to whom correspondence should be addressed.

Molecules1997, 2(6), M17;https://doi.org/10.3390/M17

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 ml), was added triethylamine (56 mg, 0.55 mmol), 4-dimethylaminopyridine (~1 mg), and 3,5-dinitrobenzoyl chloride (64 mg, 0.28 mmol) and the resultant solution allowed to stand at room temperature for 48 h. Removal of the solvent at reduced pressure gave a pale yellow oil, that was purified by flash chromatography using hexane-ethyl acetate (6:4) as eluent to afford the title compound (1) (46 mg, 45%) as pale yellow plates.

M.p. 54-56 deg.C.

IR (Nujol) cm^-1 3680-3100 (br, s, OH), 1723 (s, C=O), 1110, 1083 (s, C-O).

High Res. MS calc. for C₁₆H₁₈N₂O₉ M⁺ 382.1012, found: M+, 382.0988.

¹H-NMR (400 MHz, CDCl₃) 1.35 (1H, ddd, J_11ax,11eq 13.4, J_11ax,10ax 13.4 and J_11ax,10eq 4.8 Hz, 11ax-H), 1.41-1.72 (4H, m, 9-CH₂ and 10-CH₂), 2.01 (1H, dt, J_11eq,11ax 13.4 and J_11eq,10 2.8 Hz, 11eq-H), 2.09 (1H, dddd, J_4eq,4ax 15.3, J_4eq,5 2.5, J_4eq,3 2.5 and J_4eq,2eq 2.5 Hz, 4eq-H), 2.12 (1H, m, OH), 2.35 (1H, ddd, J_4ax,4eq 15.3, J_4ax,5 3.6 and J_4ax,3 3.6 Hz, 4ax-H), 3.44 (1H, m, 5-H), 3.56-3.67 (2H, m, 8-CH₂), 3.85 (1H, ddd, J_2ax,2eq 13.3, J_2ax,3 2.5 and J_2ax,4ax 2.5 Hz, 2eq-H), 3.95 (1H, dd, J_2eq,2ax 13.3 and J_2eq,3 1.9 Hz, 2eq-H), 5.14 (1H, m, 3-H), 9.07-9.14 (3H, m, Ar-H).

¹³C-NMR (100 MHz, CDCl₃) 18.0, 24.8, 29.5, 30.8 (CH₂, C-4, C-9, C-10 and C-11), 61.4, 61.5 (CH₂, C-2 and C-8), 68.9 (CH, C-3), 70.6 (CH, C-5), 96.5 (quat, C-6), 122.4 (CH, C-4'), 129.4 (CH, C-2' and C-6'), 133.9 (quat , C-1'), 148.6 148.7 (quat, C-3' and C-5'), 162.0 (quat, C=O).

CI-MS 382 (M⁺, 2%), 295 (40), 213 (30), 195 (80), 179 (20), 149 (60), 114 (38), 101 (100), 83 (33), 75 (65), 69 (90), 59 (20), 55 (80), 41 (59).

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgment

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

Sample Availability: No sample available.

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