The important role of trans-4-Aminocyclohexanol

According to the analysis of related databases, 27489-62-9, the application of this compound in the production field has become more and more popular.

Reference of 27489-62-9, Adding some certain compound to certain chemical reactions, such as: 27489-62-9, name is trans-4-Aminocyclohexanol,molecular formula is C6H13NO, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 27489-62-9.

Preparation of Intermediate 21) di-tert-butyl dicarbon .at?e 2) 1,1′-carbonyl trans-4-aminocyclohexanol diimidazole Intermediate 2To a 250ml flask under nitrogen atmosphere was charged DMF (98 mL) and di-t-butyl dicarbonate (63.6g, 0.291 mole). The mixture was stirred at ambient temperature to give a solution. To a second IL flask was charged tfralphakappas-4-aminocyclohexanoI (commercially available) (32.5 g, 0.285 mole) and DMF (160 mL). The mixture was heated to 55-600C to give a solution. Approximately 33% of the di-t-butyl dicarbonate in DMF solution was slowly added to the *r°/s-4-aminocyclohexanol over approximately 30 minutes, keeping the process temperature below 75C during the charge. The mixture was stirred for ~30min- 1 hour at 55-600C. The slow addition of ~33% of the di-t-butyl dicarbonate DMF solution was repeated twice more and the mixture was stirred for ~30min – 1 hour at 55-600C after each addition. After the last addition the reaction mixture was stirred at 70-750C over 1-2 hours. When GC analysis indicated that the ratio between intermediate N-Boc-frflHs-4-aminocyclohexanol and fralpha«s-4-aminocyclohexanol was greater than 33:1, the reaction mixture was cooled to 15-20C. DMF (250 mL) was charged to the reaction and stirred to give a solution. 1, 1′ -Carbonyldiimidazole (59.2g, 1.3 eq) was charged to the reaction in one portion. The reaction was stirred at ~19C for 15 hours and reaction progress was monitored by HPLC. When the HPLC analysis indicated that the ratio between Intermediate 2 and N-Boc~’««,s~4-aminocyclohexanol was greater than 49:1, the reaction mixture was cooled to ~0C. Water (600 mL) was charged slowly to the reaction mixture while keeping the process temperature below ~20C. The white solid product precipitated out of solution. The mixture was cooled to ~ 00C and stirred for 1 hour. The product was filtered and the wet cake was washed with water (100 mL) twice. The product was dried at 60-65C under vacuum to a constant weight. Yield: 82.1 g, 94%.

According to the analysis of related databases, 27489-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/62334; (2007); A2;,
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