反応 #88053

反応方程式

sodium cyanoborohydride

trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexylamine

tetrahydrofuran-3-carboxaldehyde

→

(tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine

bis-(tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine

溶媒

sodium hydrogencarbonate

methanol

acetic acid

methanol

反応条件

後処理

1. 1
   抽出the aqueous layer extracted with dichloromethane
2. 2
   乾燥The combined organic layers were dried with sodium sulfate
3. 3
   ろ過filtered
4. 4
   その他the solvent removed under reduced pressure
5. 5
   その他The crude product was purified by RP-HPLC

実験手順

To a solution of 61 mg trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexylamine (0.18 mmol) in 3 ml methanol and 0.2 ml of acetic acid at room temperature 39 mg tetrahydrofuran-3-carboxaldehyde (0.20 mmol) in 3 ml of methanol were added, and 12 mg of sodium cyanoborohydride (0.89 mmol (0.20 mmol) were then added in one portion. Stirring at room temperature was continued for 16 h. The solution was diluted with aqueous saturated sodium hydrogencarbonate solution and the aqueous layer extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and filtered, and the solvent removed under reduced pressure. The crude product was purified by RP-HPLC. 23 mg of (tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine and 19 mg of bis-(tetrahydrofuran-3-ylmethyl)-[trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-amine were isolated.

出典