At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Boc-2-(4-Aminophenyl)ethanol, and friends who are interested can also refer to it.
Application of 104060-23-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 104060-23-3 name is N-Boc-2-(4-Aminophenyl)ethanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
This compound (1.5 g, 8.6 mmol) was suspended in dry tetrahydrofuran (20 mL) at EPO 250C. The 4-(N-l-terf-butyloxycarbonyl)-aminophenethyl alcohol (3.4 g, 14.5 mmol) and triphenylphosphine (3.8 g, 14.5 mmol) were then added, and the mixture evaporated to dryness. Dry tetrahydrofuran (20 mL) was added and the suspension was cooled to 0C before dropwise addition of diethylazodicarboxylate (1.5 mL, 9.8 mmol). After 16 h reaction at room temperature, the solution was concentrated under reduced pressure. The crude residue was purified on a BIOTAGE 25M column (silica, hexane/AcOEt 95:5 to 75:25) to yield N-9 alkylated purine as a white solid (2.9 g, 87%). To a solution of alkylated 2-fluoro-6-chloropurine (3.0 g, 7.7 mmol) in n- butanol (15 mL) at 250C was added N- 1-tert-butyloxycarbonyl- 1,3 -phenyl enediamine (1.8 g, 8.8 mmol) and diisopropylethylamine (2.7 mL, 15.3 mmol). After 48 h reaction at 65C, the brown solution was concentrated under reduced pressure. The crude residue was purified on a BIOTAGE 4OM column (silica, hexane/ AcOEt 65:45 to 0:1) to yield the fluoropurine derivative as a brown solid (2.8 g, 63%). To a solution of this product (2.8 g, 4.9 mmol) in n-butanol (15 mL) at room temperature was added aminomethylcyclopropane (1.2 g, 17.1 mmol) and diisopropylethylamine (1.7 mL, 9.8 mmol). After 48 h reaction at 1100C, the brown solution was concentrated under reduced pressure. The crude residue was purified on a BIOTAGE 4OM column (silica, hexane/ AcOEt 60:40 to AcOEt/MeOH 98:2) to yield the protected trisubstituted purine as a white solid (2.3 g, 73%). To a solution of this compound (2.08 g, 3.38 mmol) in dichloromethane (10 mL) at room temperature was added 4N HCl in dioxane (10 mL). The reaction was stirred for 5 h at 25C and the solution was concentrated under reduced pressure. The solid was then dried for 16 h under vacuum to yield compound 3 as a brown solid. Yield of product: 1.4 g (quantitative); Rf = 0.1 (CH2Cl2/Me0H 98:2); 1H NMR (400 MHz, CD3OD): delta 8.24 (s, IH), 8.20-7.60 (m, 2H), 7.60-7.00 (m, 6H), 4.56 (t, 2H, J= 7.0 Hz), 3.40-3.20 (m, 4H), 1.25-1.15 (m, IH), 0.60-0.50 (m, 2H), 0.40-0.20 (m, 2H); LRMS (ESI): m/z 415 (MH+), 437 (M+ Na); HPLC (method 2): 1.6 min.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Boc-2-(4-Aminophenyl)ethanol, and friends who are interested can also refer to it.
Reference:
Patent; PROMETIC BIOSCIENCES INC.; WO2006/136005; (2006); A1;,
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