Adding a certain compound to certain chemical reactions, such as: 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, belongs to esters-buliding-blocks compound, 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 135908-33-7, Formula: C10H17NO2
Example 8 : 4- (((2- ((trans-4- (tert-butyl)c clohexyl)oxy) -4-methylnaphthalen- l-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylic acid To a mixture of 2-(cis-4-tert-butylcyclohexyloxy)-4-methyl-l-naphthaldehyde (lOOmg, 0.31 mmol, 1.0 eq) in toluene (1 mL) were added methyl 4- aminobicyclo[2.2.2]octane-l-carboxylate hydrochloride (81 mg, 0.37 mmol, 1.2 eq) and MgS04 (74 mg, 0.62 mmol, 2.0 eq). The resulting mixture was heated to reflux and stirred for 48 h. After being concentrated under reduced pressure, the residue was dissolved in THF (lmL). NaBH(OAc)3 (196 mg, 0.93 mmol, 3.0 eq) was added and the mixture was heated to reflux and stirred for 24 h. After cooling down to room temperature, the residue was diluted with EtOAc (5 mL). The suspension was filtered and the filtrate was concentrated under reduced pressure to give the residue, which was purified by column chromatography on silica gel (petroleum ether /EtOAc = 1/1) to yield the target ester (35 mg, 23 % yield) as a yellow oil. LCMS m/z 492.4 [M+H] +. Hydrolysis following standard condition gave the title compound as a white solid (20 mg, 69% yield). LCMS m/z 478.3 [M+H] +; 1H NMR (400 MHz, CD3OD) delta: 8.06- 8.01 (m, 2H), 7.61-7.59 (m, 1H), 7.49-7.47 (m, 1H), 7.36 (s, 1H), 4.54 (bs, 3H), 2.74 (s, 3H), 2.32-2.29 (m, 2H), 2.16 (bs, 12H), 1.99-1.94 (m, 2H), 1.54-1.51 (m, 2H), 1.34-1.24 (m, 2H), 1.20-1.14 (m, 1H), 0.91 (s, 9H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; LIU, Xiaogao; MA, Bin; PENG, Hairuo; WO2014/120764; (2014); A1;,
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