反応 #79580

反応方程式

(S)-(+)-1-amino-2-propanol

p-anisaldehyde

acetic acid

sodium triacetoxyborohydride

→

ammonia

title compound

(2S)-1-[(4-Methoxybenzyl)amino]-2-propanol

溶媒

methanol

反応条件

後処理

1. 1
   濃縮The reaction mixture was concentrated under reduced pressure
2. 2
   その他the residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (100 ml, 0.5N)
3. 3
   その他The layers were separated
4. 4
   抽出the aqueous phase was extracted with further dichloromethane (4×30 ml)
5. 5
   乾燥The combined organic solutions were dried (MgSO4)
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residual yellow oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane

実験手順

A mixture of (S)-(+)-1-amino-2-propanol (9 g, 0.12 mol), p-anisaldehyde (5.45 g, 0.04 mol), acetic acid (5 ml), and sodium triacetoxyborohydride (9.5 g, 0.045 mol) in methanol (80 ml) was stirred at room temperature for 72 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (100 ml, 0.5N). The layers were separated, and the aqueous phase was extracted with further dichloromethane (4×30 ml). The combined organic solutions were dried (MgSO4) and concentrated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (98:2:0.2 to 95:5:0.5) to afford the title compound, 6.2 g. 1H-NMR (CDCl3, 400 MHz) δ: 1.10 (d, 3H), 2.24-2.40 (m, 2H), 2.65 (dd, 1H), 3.62-3.80 (m, 6H), 6.82 (d, 2H), 7.19 (d, 2H). LRMS: m/z (ES+) 218 [MNa+]

出典