Ortho-chiral amino alcohol compound under benzyl protection and preparation method thereof
A technology of chiral amino alcohols and compounds, applied in organic chemistry methods, preparation of sulfonic acid amides, organic chemistry, etc., can solve the problems of limited applicable groups, low selectivity, high cost, etc., achieve high yield, simple operation, The effect of simple routes
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Embodiment 1
[0020] Synthesis of compound 3a
[0021] Under the protection of nitrogen, compound 1a (150mg, 0.87mol) was dissolved in tetrahydrofuran (2mL), and added to the newly prepared samarium diiodide (0.1M, 35mL), and then 2-(phenoxymethyl) pyridine sulfone was added dropwise Tetrahydrofuran solution (457.6 mg, 2 mol), stirred at room temperature for 40 minutes, quenched with water, added anhydrous magnesium sulfate, stirred, filtered through a silica gel funnel, washed once with saline, dried over anhydrous magnesium sulfate, filtered and concentrated, and subjected to silica gel column chromatography Compound 3 was obtained as a colorless oil (135 mg, 56%). 1 H NMR (400MHz, CDCl 3 ,rotamers)7.37-7.27(m,5H),4.62-4.51(m,1H),4.51-4.46(m,1H),3.67-3.61(m,0.75H),3.56-3.48(m,1H),3.48 -3.43(m,0.75H),3.43-3.33(m,1.5H),1.71-1.65(m,1H),1.62-1.49(m,0.9H),1.49-1.41(m,1.1H),1.40- 1.37(m,1H),1.25-1.16(m,9H),0.97-0.88(m,3H)ppm.
[0022] Synthesis of compound 3b
[0023] Under the protection ...
Embodiment 2
[0063] The preparation of compound 3b-u was the same as in Example 1.
[0064] Synthesis of compound 3a
[0065] Under nitrogen protection, compound 1a (150 mg, 0.87 mol) was dissolved in tetrahydrofuran (2 mL), and azobisisobutyronitrile (428 mg, 2.6 mol) was added, followed by dropwise addition of 2-(phenoxymethyl) pyridine sulfone Tetrahydrofuran solution (457 mg, 2 mol), stirred at room temperature for 1 h, quenched with water, added anhydrous magnesium sulfate, stirred, filtered through a silica gel funnel, washed with saline once, dried over anhydrous magnesium sulfate, filtered and concentrated, and obtained by silica gel column chromatography. Compound 3a (95 mg, 42%) as a colored oil.
Embodiment 3
[0067] The preparation of compound 3b-u was the same as in Example 1.
[0068] Synthesis of compound 3a
[0069]Under nitrogen protection, compound 1a (150 mg, 0.87 mol) was dissolved in tetrahydrofuran (2 mL), and dibenzoyl peroxide (629 mg, 2.6 mol) was added, followed by dropwise addition of 2-(phenoxymethyl)pyridine sulfone Tetrahydrofuran solution (457 mg, 2 mol), stirred at room temperature for 1 h, quenched with water, added anhydrous magnesium sulfate, stirred, filtered through a silica gel funnel, washed with saline once, dried over anhydrous magnesium sulfate, filtered and concentrated, obtained by silica gel column chromatography Compound 3a (112 mg, 50%) as a colored oil.
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