The origin of a common compound about 3,4-Dihydro-2H-benzo[b][1,4]oxazin-6-ol

According to the analysis of related databases, 26021-57-8, the application of this compound in the production field has become more and more popular.

Synthetic Route of 26021-57-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 26021-57-8, name is 3,4-Dihydro-2H-benzo[b][1,4]oxazin-6-ol. This compound has unique chemical properties. The synthetic route is as follows.

a) (S)-3-(3,4-Dihydro-2H-benzo[1,4]oxazin-6-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester A solution of 3,4-dihydro-2H-benzo[1,4]oxazin-6-ol (CAS registry 26021-57-8) (4.0 g, 26.5 mmol) in DMF (150 ml) was treated with NaH (2.117 g, 52.9 mmol) for 20 min at 20 C. (R)-3-Methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (CAS registry 127423-61-4) (9.13 g, 34.4 mmol) was added. After stirring for 22 h at rt the reaction mixture was concentrated to dryness, then taken up with EtOAc, filtered through hyflo and the filtrate was washed with sat. aq. Na2CO3 solution. Combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (cyclohexane/isopropanol 100:0 to 85:15 in 40 min) to provide the title compound as a yellow oil. HPLC RtM8=1.84 min; ESIMS: 321 [(M+H)+]. 1H NMR (400 MHz, DMSO): 6.52 (d, 1H), 6.12 (d, 1H), 6.02 (m, 1H), 5.76 (m, 1H), 4.75 (br s, 1H), 4.01-40.5 (m, 2H), 3.27-3.50 (m, 4H), 3.22-3.26 (m, 2H), 1.95-2.08 (m, 2H), 1.39 (m, 9H).

According to the analysis of related databases, 26021-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
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