These common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, its 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. category: esters-buliding-blocks
Step 9; methyl ll-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-10-methyl-2-oxo-2,5,6,7,8,10-hexahydro-lH- pyrido [3 ‘,2’ : 7,8] cycloocta [1,2-f] indole-3-carboxylate Crude N-(2-((tert-butyldimethylsilyloxy)methyl)- 1 -methyl-7,8,9, 10-tetrahydro- 1 H- cycloocta[f]indol-5(6H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (-0.60 g, 1.17 mmol) and trimethyl methanetricarboxylate (0.37 g, 1.95 mmol) were mixed together in Ph 0 (2.5 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature). The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes, followed by EtOAc/hexanes 0-60% gradient) to yield the product as a yellow foam (0.3750 g, 51%, 2 steps). XH NMR (500 MHz, CHCl3-i/) delta ppm 0.10 (s, 3 H) 0.11 (s, 3 H) 0.91 (s, 9 H) 1.33 – 1.51 (m, 3 H) 1.80 – 1.90 (m, 1 H) 2.02 (t, J=7.7 Hz, 1 H) 2.13 (t, J=12.0 Hz, 1 H) 2.55 (dd, J=13.6, 7.3 Hz, 1 H) 2.82 (dd, J=13.2, 7.6 Hz, 1 H) 3.10 (s, 3 H) 3.76 (s, 3 H) 3.77 (s, 3 H) 4.03 (s, 3 H) 4.80 (d, J=13.2 Hz, 1 H) 4.82 (d, J=13.2 Hz, 1 H) 4.96 – 5.26 (m, 2 H) 6.12 (d, J=2.5 Hz, 1 H) 6.24 (s, 1 H) 6.32 (dd, J=8.5, 2.2 Hz, 1 H) 6.81 (d, J=8.5 Hz, 1 H) 7.04 (s, 1 H) 7.11 (s, 1 H) 13.73 (s, 1 H). LC-MS 647.5 [M+H]+, RT 1.90 min.
The synthetic route of Trimethyl methanetricarboxylate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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