تفاعل #428167

معادلة التفاعل

K2CO3

(S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea

t-BuOH

water

→

1-((2S,4R)-1-(tert-butyldimethylsilyloxy)-4,5-dihydroxypentan-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea

المردود 55.0%

المذيبات

t-BuOH water

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to 0° C
2. 2
   workup.ADDITIONTo the mixture was added
3. 3
   workup.STIRRINGthe reaction was stirred at 0° C. overnight
4. 4
   workup.STIRRINGthe reaction was stirred at RT for 30 min
5. 5
   غسيلwashed with water (250 mL×2) and brine (250 mL)
6. 6
   تجفيفdried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزThe filtrate was concentrated
9. 9
   أخرىpurified on silica gel

الإجراء التجريبي

To a mixture of t-BuOH (300 mL) and water (300 mL) were added K2CO3 (17.0 g, 123 mmol,), (DHQD)2Pyr (361 mg, 0.41 mmol), K2OsO2(OH)4(151 mg, 0.41 mmol), K3FeCN6 (40.5 g, 123 mmol) at RT The mixture was stirred at RT for 2 h and then cooled to 0° C. To the mixture was added a suspension of (S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea (17.0 g, 41 mmol) in 100 mL of t-BuOH/water (1:1), and the reaction was stirred at 0° C. overnight. LC-MS indicted the reaction was completed, Na2S2O3.5H2O (30.6 g, 123 mmol) was added to the reaction, and the reaction was stirred at RT for 30 min. The mixture was diluted with ethyl acetate (1 L), washed with water (250 mL×2) and brine (250 mL), dried over Na2SO4, and filtered. The filtrate was concentrated and purified on silica gel to give 1-((2S,4R)-1-(tert-butyldimethylsilyloxy)-4,5-dihydroxypentan-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea (10.1 g, 55%) as a colorless oil.

المصدر