تفاعل #86288

معادلة التفاعل

3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)aniline

2-(methyldithio)isobutyraldehyde

sodium triacetoxyborohydride

magnesium sulfate

Sodium triacetoxyborohydride

→

3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-(2-methyl-2-(methyldisulfanyl)propyl)aniline

المردود 41.7%

المذيبات

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGto stir at ambient temperature for 20 hours
2. 2
   ترشيحThe mixture was filtered
3. 3
   غسيلthrough celite rinsing with dichloromethane
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   استخلاصthen extracted with ethyl acetate and water
6. 6
   غسيلThe organic extracts were washed with brine
7. 7
   تجفيفdried over magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىpurified by combiflash (EtOAc/Hex)

الإجراء التجريبي

To a solution of 3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)aniline (6.7 g, 12.69 mmol) in anhydrous 1,2-dichloroethane (50 ml) was added 2-(methyldithio)isobutyraldehyde (2.74 ml, 19.04 mmol), sodium triacetoxyborohydride (2.8g, 1 eq), zinc(II) chloride (0.865 g, 6.35 mmol) and magnesium sulfate (2.292 g, 19.04 mmol). The mixture was stirred for five hours at ambient temperature. Sodium triacetoxyborohydride (2.8g, 1 eq) was added. The reaction continued to stir at ambient temperature for 20 hours. The mixture was filtered through celite rinsing with dichloromethane and concentrated under reduced pressure then extracted with ethyl acetate and water. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, concentrated and purified by combiflash (EtOAc/Hex) to give 3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-(2-methyl-2-(methyldisulfanyl)propyl)aniline (3.5g, 40%). 1H NMR (400 Hz, CDCl3): δ 6.73 (s, 2H), 6.59 (s, 1H), 4.56 (s, 4H), 3.65-3.51 (m, 14H), 3.30 (s, 3H), 2.38 (s, 3H), 1.28 (s, 6H), 0.84 (s, 18H), 0.00 (s, 12H). MS (m/z). found 684.2 (M+Na)+. See FIG. 46.

المصدر