Synthetic process of chiral 2-amido-1-(6-fluorine-3,4-dihydrobenzopyranyl) alCohol
A technology of dihydrobenzopyranyl and synthesis method, applied in directions such as organic chemistry, can solve problems such as low product purity, high production cost, harsh conditions and the like
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Embodiment 1
[0022] (1). Synthesis of (R)-1-((R)-6-fluoro-3,4-dihydrochromenyl)ethane-1,2-diol (2a):
[0023] In the reactor, add compound 1a and freshly prepared zinc amalgam (molar ratio, 1: 120), hydrochloric acid (40ml), 48ml ethanol, stir and react for 50 hours, then add hydrochloric acid (20ml), react for 6 hours, and cool , filtered, the filtrate was extracted with ethyl acetate, washed with saturated brine until neutral, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain viscous liquid (R)-1-((R)-6-fluoro-3, 4-Dihydrochromenyl)ethane-1,2-diol (2a).
[0024] (2).(R)-2-((R)-6-fluoro-3,4-dihydrochromenyl)-2-hydroxyethyl-4-methylbenzenesulfonate (3a) synthesis:
[0025] In the reactor, add (R)-1-((R)-6-fluoro-3,4-dihydrobenzopyranyl)ethane-1,2-diol (2a), add 10ml pyridine to dissolve , stirred, then added p-toluenesulfonyl chloride (mole ratio, 2a: p-toluenesulfonyl chloride=1:1.0), reacted for 48 hours, then, added 10ml of ice water to the reaction syste...
Embodiment 2
[0029] (1). Synthesis of (R)-1-((R)-6-fluoro-3,4-dihydrochromenyl)ethane-1,2-diol (2a):
[0030] In the reactor, add compound 1a, freshly prepared zinc amalgam (molar ratio, 1a:zinc amalgam=1:1.2), 60ml hydrochloric acid, 48ml ethanol, stir and react for 46 hours, then add 30ml hydrochloric acid and react for 6 hours , cooled, filtered, extracted filtrate, washed with saturated brine until neutral, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain viscous liquid (R)-1-((R)-6-fluoro-3,4- Dihydrochromenyl)ethane-1,2-diol (2a).
[0031] (2).(R)-2-((R)-6-fluoro-3,4-dihydrochromenyl)-2-hydroxyethyl-4-methylbenzenesulfonate (3a) synthesis:
[0032] In the reactor, add (R)-1-((R)-6-fluoro-3,4-dihydrochromenyl)ethane-1,2-diol (2a), add 15ml pyridine to dissolve , stirred, then added p-toluenesulfonyl chloride (molar ratio, 2a: p-toluenesulfonyl chloride=1:1.4), stirred and reacted for 24 hours, added 10ml of ice water to the reaction system, extracted w...
Embodiment 3
[0036] (1). Synthesis of (S)-1-((R)-6-fluoro-3,4-dihydrochromenyl)ethane-1,2-diol (2b):
[0037] In the reactor, add compound and freshly prepared zinc amalgam (molar ratio, 1:110), 90ml hydrochloric acid, 48ml ethanol, stir and react for 50 hours, then add dilute hydrochloric acid, react for 6 hours, cool, filter, and extract the filtrate , washed with saturated brine until neutral, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain viscous liquid (S)-1-((R)-6-fluoro-3,4-dihydrobenzopyranyl ) Ethane-1,2-diol.
[0038] (2).(R)-2-((S)-6-fluoro-3,4-dihydrochromenyl)-2-hydroxyethyl-4-methylbenzenesulfonate (3b) synthesis:
[0039] In the reactor, add (S)-1-((R)-6-fluoro-3,4-dihydrochromenyl)ethane-1,2-diol (2b), add pyridine to dissolve, Stir, then add p-toluenesulfonyl chloride (molar ratio, 2b: p-toluenesulfonyl chloride=1:1.01), stir for 24 hours, then add 10ml of ice water to the reaction system to terminate the reaction, extract, wash with dilu...
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