Реакция #51962

Уравнение реакции

4-[(dimethylamino)methyl]benzaldehyde

ammonium chloride

tert-butyl dimethylcarbamate

tetramethylethylenediamine

sec-butyllithium

→

title compound

Выход 76.3%

tert-Butyl 2-{4-[(dimethylamino)methyl]phenyl}-2-hydroxyethyl(methyl)carbamate

Выход 76.3%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas introduced
2. 2
   workup.STIRRINGstirred for 1 hour
3. 3
   Другоеto quench
4. 4
   Другоеthe reaction after the reaction mixture
5. 5
   Температураwas cooled to −78° C
6. 6
   ДругоеThe organic phase was separated
7. 7
   Экстракцияthe aqueous phase was extracted with dichloromethane
8. 8
   Промывкаwashed with brine
9. 9
   Сушкаdried over sodium sulfate
10. 10
    Концентрированиеconcentrated
11. 11
    ДругоеThe residue was purified with a silica gel column

Методика

To a solution of tert-butyl dimethylcarbamate (350 mg, 2.4 mmol) and tetramethylethylenediamine (511 mg, 4.4 mmol) in THF (anhydrous, 10 mL) was added sec-butyllithium (1.4 M in cyclohexane, 2.2 mL, 3.1 mmol) at −78° C. The mixture was stirred at that temperature for 1 hour before 4-[(dimethylamino)methyl]benzaldehyde (J.Heterocycl.Chem.; 26; 1989; 1325-1330)(280 mg, 1.7 mmol) was introduced. The reaction mixture was stirred for 2 hours, warmed to room temperature and stirred for 1 hour. Saturated ammonium chloride aqueous solution (10 mL) was added to quench the reaction after the reaction mixture was cooled to −78° C. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with brine and dried over sodium sulfate and concentrated. The residue was purified with a silica gel column to give the title compound (0.40 g) as a white solid.

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