反応 #42421

反応方程式

methanesulfonyl chloride

methyl 3-(hydroxymethyl)-5-methylbenzoate

Butylamine

triethylamine

→

title compound

Methyl 3-[(butylamino)methyl]-5-methylbenzoate

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   ろ過filtered
2. 2
   workup.STIRRINGthe reaction mixture is stirred at room temperature for 5 h
3. 3
   洗浄washed with 1 N hydrochloric acid, and saturated sodium bicarbonate
4. 4
   乾燥dried (magnesium sulfate)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他Purification by flash column chromatography (silica, 89:10:1 chloroform/methanol/ammonium hydroxide)

実験手順

To an ice-cold, stirred solution of methyl 3-(hydroxymethyl)-5-methylbenzoate (200 mg, 1.1 mmol) in methylene chloride (2.2 mL) is added triethylamine (0.304 mL, 2.2 mmol) followed by methanesulfonyl chloride (0.116 mL, 1.5 mmol). The reaction mixture is stirred for 15 min and filtered. Butylamine (0.543 mL, 5.5 mmol) is added to the filtrate, and the reaction mixture is stirred at room temperature for 5 h. The reaction mixture is diluted with methylene chloride (10 mL), washed with 1 N hydrochloric acid, and saturated sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 89:10:1 chloroform/methanol/ammonium hydroxide) provides the title compound. 1H NMR (300 MHz, CDCl3) δ 7.75 (s, 1H), 7.70 (s, 1H), 7.24 (br s, 1H), 4.42 (d, J=9 Hz, 2H), 3.90 (s, 3H), 3.16 (m, 2H), 2.38 (s, 3H), 1.64 (s, 2H), 1.44 (m, 9H), 1.27 (m, 2H), 0.89 (t, J=7 Hz, 3H).

出典