反応 #164110

反応方程式

acetic acid

formalin

title compound

C-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-methylamine

sodium cyanoboron hydride

→

Dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-ylmethyl)-amine

溶媒

chloroform methanol

acetonitrile

反応条件

後処理

1. 1
   その他a cloudy solution was formed
2. 2
   濃縮concentrated to low volume in a vacuum
3. 3
   洗浄washed with NaHCO3 solution
4. 4
   抽出the aqueous phase extracted with ether
5. 5
   乾燥The combined organic phases were dried over Na2SO4
6. 6
   濃縮concentrated to low volume in a vacuum
7. 7
   その他The raw product was purified by flash chromatography with chloroform/methanol (50:1→20:1→9:1)

実験手順

The title compound of step 4 (5.40 g, 21.8 mmol) was dissolved in acetonitrile (150 mL), and a cloudy solution was formed. Aqueous 37% formalin solution (30.6 mL, 407 mmol) was added. The batch was stirred for 20 min at RT and then mixed with sodium cyanoboron hydride (5.76 g, 91.7 mmol). The reaction was followed by DC in chloroform/methanol (9:1). After 4 h the solution was adjusted to pH 7 with acetic acid and concentrated to low volume in a vacuum. The residue was taken up in chloroform, washed with NaHCO3 solution and the aqueous phase extracted with ether. The combined organic phases were dried over Na2SO4 and concentrated to low volume in a vacuum. The raw product was purified by flash chromatography with chloroform/methanol (50:1→20:1→9:1).

出典