Synthetic Route of 16355-92-3,Some common heterocyclic compound, 16355-92-3, name is 1,10-Diiododecane, molecular formula is C10H20I2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 26 (n=10); (a) 1,1′-[(Decane-1,10-diyl)idoxy]bis[(11S,11aS)-10-(tert- butyloxycarbonyl)-7-methoxy-11- (tetrahydro-pyran-2-yloxy)-2- methylidene-1, 2, 3, 10, 11, 11a-hexahydro-5H-pyrrolo [2, 1- c] [1, 4] benzodiazepine-5-one] (28c); 1,10-Diiododecane (49.26 mg, 0.125 mmol, 0.5 equiv. ) was added to the mixture of monomer 27 (115 mg, 0.25 mmol, 1.0 equiv. ) and potassium carbonate (53 mg, 0.50 mmol, 2.0 equiv. ) in dry DMF (30 mL), and the resulting mixture was heated to 90 C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (Si02, 60% EtOAc-hexane) to afford the dimerized compound 28c (90 mg, 0.084 mmol, 67% yield, mixture of diastereomers from THP protecting group) as a solid: [ (X] 21, = +22 (c = 0.11, CHC13) ; 1H NMR (CDCl3, 400 MHz): 5 1. 26-1. 65 (m, 76H, 14-H, 15-H, 16-H, Boc, THP), 1.72-1. 90 (m, 16H, 13-H, THP), 2.55- 2.95 (m, 8H, 1-H), 3.53-3. 69 (m, 8H, lla-H, THP), 3.85-4. 15 (m, 28H, 3-H, 12-H, 7-OMe, THP), 4.25-4. 36 (m, 4H, 3-H), 4.97-5. 18 (m, 12H, 2a-H, THP), 5. 65-5. 88 (m, 4H, 11-H), 6.48 (s, 3H, 9-H), 6.85 (s, 1H, 9-H), 7.15-7. 19 (2 x s, 4H, 6-H) ; 13 C NMR (CDC13, 100 MHz): 5 20. 0,20. 5,25. 2,25. 9,28. 1,28. 2,29. 0,29. 4,29. 5,31. 0, 31. 3,35. 1,35. 4,50. 6,56. 1, 60.0, 63.5, 64.4, 68.9, 69.2, 91.1, 96.4, 100.3, 109.4, 110. 0,110. 6,114. 3, 114. 9,128. 4,142. 1, 148.8, 149.3, 167.3 ; IR (neat): 2933,2854, 1703,1643, 1603, 1512,1454, 1430, 1402,1367, 1324,1254, 1209,1162, 1118,1018, 910,860, 729 cm-1 ; MS (ES+) m/z (relative intensity) 1059 ([M + H] +, 100), 1060 ( [M + 2H] +, 70), 957 (50).
The synthetic route of 16355-92-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com