反応 #2446084

反応方程式

1-(cyclohexylamino)-propan-2-ol

HCHO

Na(OAc)3BH

acetic acid

→

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

溶媒

ethyl acetate

NaOH

DCE

反応条件

後処理

1. 1
   その他The organic layer was separated
2. 2
   洗浄washed with water and brine
3. 3
   乾燥dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The crude material was purified by chromatography on silica-gel (230-400 mesh)
7. 7
   洗浄eluting with 5% MeOH/DCM

実験手順

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).

出典