반응 #479337

반응 방정식

(2S)-(2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl)-[3-(5-fluoro-1H-indol-3-yl)-propyl]-amine

formaldehyde

sodium cyanoborohydride

acetic acid

→

title compound

N-(2,3-Dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl)-N-[3-(5-fluoro-1H-indol-3-yl)propyl]-N-methylamine

용매

methanol

반응 조건

후처리

1. 1
   기타quenched with 1N NaOH (5 mL)
2. 2
   추출The mixture was extracted with methylene chloride (3×50 mL)
3. 3
   세척The organic layer was washed with water (3×50 mL)
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   여과filtered
6. 6
   기타the solvent was removed under vacuum
7. 7
   기타chromatographed on silica gel (5% methanol-methylene chloride)
8. 8
   농축The product-containing fractions were concentrated in vacuum

실험 절차

To a solution of (2S)-(2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl)-[3-(5-fluoro-1H-indol-3-yl)-propyl]-amine (0.13 g, 0.33 mmol) and formaldehyde (37 wt. % in water, 0.26 g, 3.3 mmol) in methanol (20 mL) was added sodium cyanoborohydride (0.038 g, 0.59 mmol) and acetic acid (0.03 g, 0.5 mmol) at room temperature. The mixture was stirred at room temperature under nitrogen overnight, then quenched with 1N NaOH (5 mL). The mixture was extracted with methylene chloride (3×50 mL). The organic layer was washed with water (3×50 mL), dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum. The crude oil was column chromatographed on silica gel (5% methanol-methylene chloride). The product-containing fractions were concentrated in vacuum to give 0.1 g of the (S)-enantiomer of the title compound as a brown oil. The dihydrochloride salt was prepared in ethyl acetate as a yellow solid (decomposed at 78° C.).

출처