Related Products of 63485-50-7, These common heterocyclic compound, 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, 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.
8-0I (Intermediate 126A) (380 mg, 2.23 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to 0 C, and methyl 3-hydroxycyclobutanecarboxylate (0.37 mL, 3.5 mmol) was added, followed by DIAD (0.68 mL, 3.5 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-1 00% EtOAc-hexanes gradient to give a mixture of cis and trans isomers which were separated on an IC 30 X 250 mm column eluting with 50% EtOH in hexanes to give the title compound (137 mg, 21 %). 1H NMR (400 MHz, CD3SOCD3) delta 2.48- 2.59 (m, 2 H), 2.82 (ddd, J = 14, 7, 5 Hz, 2 H), 3.22-3.32 (m, 1 H), 3.31 (s, 3 H), 5.07 (t, J = 7 Hz, 1 H), 6.91 (dd, J = 1 1 , 3 Hz, 1 H), 7.31 (dd, J = 9, 3 Hz, 1 H), 7.59 (dd, J = 8, 4 Hz, 1 H), 8.30 (dd, J = 8, 2 Hz, 1 H), 8.83 (dd, J = 4, 2 Hz, 1 H); LC-MS (LC-ES) M+H = 276.
Statistics shows that cis-Methyl 3-hydroxycyclobutanecarboxylate is playing an increasingly important role. we look forward to future research findings about 63485-50-7.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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