146307-51-9 Archives - Esters-buliding-blocks

Introduction of a new synthetic route about C13H23NO4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, its application will become more common.

Application of 146307-51-9,Some common heterocyclic compound, 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, molecular formula is C13H23NO4, 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.

Step 2 trans-Methyl 4-((tert-butoxycarbonyl)(methyl)amino)cyclohexanecarboxylate To a solution of trans-methyl 4-((tert-butoxycarbonyl)amino)cyclo hexanecarboxylate (1.7 g, 6.6 mmol) in DMF (50 mL) was added NaH (1.05 g, 26.4 mmol, 60% in mineral) at room temperature. The reaction mixture was stirred at room temperature for 1 h. Iodomethane (9.9 g, 69.7 mmol) was added into the reaction mixture and the reaction mixture was stirred at room temperature for 18 h. TLC (PE / EtOAc = 4 : 1) showed the starting material has been consumed. The mixture was neutralized with HCl (2N) till pH ~7. The reaction mixture was added into 100 mL of water. The aqueous was extracted with EtOAc (70 mL x 2). The combined organic layers were dried over anhydrous (1204) Na2S04 and concentrated in vacuum to give trans-methyl 4-((tert- butoxycarbonyl)(methyl)amino)cyclo hexanecarboxylate (1.3 g, yield 72%) as a colorless oil.

Reference:
Patent; BIOGEN MA INC.; KUMARAVEL, Gnanasambandam; PENG, Hairuo; XIN, Zhili; WO2015/188051; (2015); A1;,
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Some tips on 146307-51-9

These common heterocyclic compound, 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, 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. SDS of cas: 146307-51-9

Reference Example 2;: Trans-4-(2-oxopyrrolidin-1-yl)cyclohexanecarboxylic acid ; [] (1) Methyl trans-4-[(t-butoxycarbonyl)amino]-cyclohexanecarboxylate (234.0 g) obtained in Reference Example 1 is dissolved in dioxane (500 ml), and thereto is added 4 N hydrogen chloride/dioxane (500 ml), and the mixture is stirred at room temperature for 19 hours. The reaction solution is concentrated under reduced pressure, and the resulting residue is suspended in diethyl ether. The precipitates are collected by filtration to give methyl trans-4-aminocyclohexanecarboxylate hydrochloride (121.9 g). APCI-MS M/Z:158[M+H]+.;

The synthetic route of trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Research on new synthetic routes about 146307-51-9

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a solution of (frans)-methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate (Intermediate 18A) (1 .5 g, 5.8 mmol) in EtOH (24 mL) and THF (2.7 mL), cooled on ice, was added calcium chloride (1 .29 g, 1 1 .7 mmol) portion wise to give a milky suspension. NaBH4 (882 mg, 23.3 mmol) was then added portion wise over ca. 25 min and the reaction was stirred on ice for 1 h. The bath was removed and the mixture was allowed to stir at room temperature overnight. The reaction was cooled to 10 C and to this was added 5% aqueous K2CO3 (5.4 mL) dropwise, to give a pH of ca. 1 1 . A white precipitate formed and was isolated by filtration. The solid was stirred with EtOAc (50 mL) and water (14 mL). The layers were separated and the organic layer was washed with 0.5 M aqueous HCI (5 mL), water and brine, dried over MgS04, filtered, and concentrated to give the title compound (474 mg) as a white solid. The initial filtrate was concentrated, then dilute with saturated aqueous NH4CI and extracted with EtOAc (3X). Combined organics were washed with brine and dried over Na2SC>4, filtered, and concentrated to give the title compound (724 mg) as a white solid. Total isolated product was 1 .1 9 g (89% yield). 1H NMR (400 MHz, CD3SOCD3) delta 0.78-0.93 (m, 2 H), 1 .01 -1 .15 (m, 2 H), 1 .35 (s, 9 H), 1 .64-1 .80 (m, 4 H), 3.10 (d, J = 8 Hz, 1 H), 3.16 (t, J = 6 Hz, 2 H), 4.33 (t, J = 5 Hz, 1 H), 6.64 (d, J = 8 Hz, 1 H).

According to the analysis of related databases, 146307-51-9, the application of this compound in the production field has become more and more popular.

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The important role of C13H23NO4

Step 2: Trans-tert-butyl 4-(hydroxymethyl)cyclohexylcarbamateMethyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate (55.5 g, 216 mmol) was suspended in ethanol (900 ml) and THF (100 ml) and the mixture was cooled to 5C. Granular calcium chloride (47.9g, 431 mmol) was added portionwise to give a milky suspension. Sodium borohydride (32.6 g, 863 mmol) was added portionwise over 25 mins at 5C. The reaction mixture (white emulsion) was stirred at 5C for 1 hour, the water bath was removed and then the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture was cooled to 10C and 5% potassium carbonate (200 ml) was added dropwise until the pH of the solution was pH11. A colourless precipitate formed which was filtered off. The solid was stirred with ethyl acetate (2000 ml) and water (500 ml). The organic layer was separated and washed with 0.5M HCI (200 ml), then washed with water (2 x 200 ml) and saturated brine (100 ml). The organic solution was dried over anhydrous MgS04, filtered and evaporated to give a white solid The solid was dried under high vacuum overnight to constant weight; [M+H]+230.

According to the analysis of related databases, 146307-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ATKINSON Benjamin; BEATTIE David; CULSHAW Andrew James; DEVEREUX Nicholas James; MCKENNA Jeffrey; DALE James; WO2011/92293; A1; (2011);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics