Реакция #2446084

Уравнение реакции

1-(cyclohexylamino)-propan-2-ol

HCHO

Na(OAc)3BH

acetic acid

→

1-(cyclohexyl(methyl)amino)propan-2-ol

Растворители

ethyl acetate

NaOH

DCE

Условия реакции

Обработка

1. 1
   ДругоеThe organic layer was separated
2. 2
   Промывкаwashed with water and brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe crude material was purified by chromatography on silica-gel (230-400 mesh)
7. 7
   Промывкаeluting with 5% MeOH/DCM

Методика

To a stirred solution of 1-(cyclohexylamino)-propan-2-ol (crude 2.6 g) in DCE (30 mL) were added successively HCHO (35% in water, 2.1 mL, 24.8 mmol), Na(OAc)3BH (10.5 g, 49.6 mmol) and acetic acid (1 mL) at ice-cold conditions. The resulting mixture was allowed to stir at rt for 16 hours. The reaction was diluted with ethyl acetate and basified with 1N NaOH. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on silica-gel (230-400 mesh) eluting with 5% MeOH/DCM to provide 1-(cyclohexyl(methyl)amino)propan-2-ol. Yield: 1.0 g 1H NMR (DMSO-d6) δ 4.11 (brs, 1 H), 3.65-3.57 (m, 1 H), 2.35-2.20 (m, 3 H), 2.19 (s, 3 H), 1.72-1.68 (m, 4 H), 1.57-1.54 (m, 1 H), 1.24-1.05 (m, 5 H), 1.01 (d, J=6 Hz, 3 H).

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