(5-methyl-1,3-dioxan-5-yl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A deareated solution of 5-(hydroxymethyl)-5-methyl-1,3-dioxane (1.19 g, 9 mmol) in 125 ml dry THF was treated with NaH (0.79 g 55% dispersion in oil, 18 mmol) for 20 min. 4-Chloro-3-methoxy-2-methylpyridine-N-oxide (1.04 g, 6 mmol) was added and the mixture was refluxed for 26 h. Excess NaH was quenched with 10 ml of H2O and the solvent evaporated. The residue was partitioned between 150 ml CH2Cl2 and 50 ml 5% Na2CO3. The organic layer was passed through a phase separation paper and evaporated leaving 1.83 g enriched product. Chromatography (SiO2CH2Cl2 /MeOH, 95/5) afforded 0.39 g (24%) pure title compound as a tanned oil. the mixture was refluxed for 26 h Excess NaH was quenched with 10 ml of H2O the solvent evaporated The residue was partitioned between 150 ml CH2Cl2 and 50 ml 5% Na2CO3 The organic layer was passed through a phase separation paper evaporated leaving 1.83 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid and 5-methyl-[1,3]dioxan-5-ylmethanol according to the procedure of Example 1 as an off-white solid; 1H NMR (DMSO-d6,400 MHz) 6 0.7 (s, 3H, CH3), 0.74 (s, 3H, CH3), 1.1 (d, J=6.59 Hz, 3H, CH3), 2.6 (m, 1H, CH), 3-3.3 (m, 8H, CH, CH2), 3.6-3.7 (m, 4H, CH2), 4.6-4.8 (m, 4H, CH2), 5.04 (m, 1H, CH), 6.34 (brs, 1H, OH), 6.84 (dd, J=8.13, 1.32 Hz, 1H, Ar--H), 7.07 (m, 2H, Ar--H), 7.36-7.44 (m, 3H, Ar--H), 7.48 (s, 1H, Ar--H), 8.77 (brs, 1H, NH), 9.2 (brs, 1H, NH); IR (KBr, cm-) 3400 (OH), 2900 (NH), 1760 (CO); MS m/e 650 (M+H)+; Analysis for: C32H40ClNO11 ×HCl: Calc'd: C, 55.98; H, 6.02; N, 2.04; Found: C, 54.67; H, 6.58; N, 2.05.