Реакция #2254205

Уравнение реакции

2-[4-(4-fluorophenyl)oxan-4-yl]ethan-1-amine

benzaldehyde

→

benzyl({2-[4-(4-fluorophenyl)oxan-4-yl]ethyl})amine

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction mixture was filtered
2. 2
   Концентрированиеconcentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 5 ml MeOH at 0° C.
4. 4
   workup.ADDITIONNaBH4 added in one portion (51 mg, 1.34 mmol)
5. 5
   workup.STIRRINGThe reaction was stirred at 0° C. for 1 h
6. 6
   ДругоеThe solution was then quenched with H2O (10 ml)
7. 7
   Экстракцияextracted with CH2Cl2 (3×20 ml)
8. 8
   Промывкаwashed with brine (10 ml)
9. 9
   Другоеdried over NA2SO4
10. 10
    ДругоеPurified by normal phase SiO2 chromatography (0 to 10% MeOH/CH2Cl2)

Методика

To a solution of 2-[4-(4-fluorophenyl)oxan-4-yl]ethan-1-amine (250 mg, 1.12 mmol) in anhydrous CH2Cl2 (5 ml) and NA2SO4 (159 mg, 1.12 mmol) at rt was added benzaldehyde (0.17 ml, 1.68 mmol). The reaction was stirred overnight. The reaction mixture was filtered and concentrated. The residue was dissolved in 5 ml MeOH at 0° C. and NaBH4 added in one portion (51 mg, 1.34 mmol). The reaction was stirred at 0° C. for 1 h. The solution was then quenched with H2O (10 ml), extracted with CH2Cl2 (3×20 ml), washed with brine (10 ml) and dried over NA2SO4. Purified by normal phase SiO2 chromatography (0 to 10% MeOH/CH2Cl2) to give benzyl({2-[4-(4-fluorophenyl)oxan-4-yl]ethyl})amine as a colorless oil (200 mg, 60%, m/z: 314.2 [M+H]+ observed).

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