반응 #1266259

반응 방정식

sodium triacetoxyborohydride

4-dimethylamino-4-phenylcyclohexanone

sodium sulfate

dihydrochloride

HCl

Serotonin

→

3-[2-(4-Dimethylamino-4-phenyl-cyclohexylamino)-ethyl]-1H-indol-5-ol dihydrochloride

용매

acetic acid

ethanol 2-butanone

1,2-dichloroethane THF

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas carried out for a further two days
3. 3
   농축the mixture was concentrated
4. 4
   workup.ADDITIONwater (10 ml) and 2M HCl (1 ml), further diethyl ether (20 ml) was added
5. 5
   기타the organic phase was coarsely separated off
6. 6
   추출extracted with ethyl acetate (3×5 ml)
7. 7
   추출again extracted with ethyl acetate (5×10 ml)
8. 8
   기타The organic extracts were dried
9. 9
   농축concentrated
10. 10
    기타the residue was purified by flash chromatography (eluant: MeOH/NEt3 99.5:0.5)
11. 11
    기타267 mg of the nonpolar diastereomer (m.p. 90-100° C.) were isolated

실험 절차

Serotonin (405 mg) was dissolved in 1,2-dichloroethane/THF (5 ml/20 ml), and 4-dimethylamino-4-phenylcyclohexanone (500 mg), glacial acetic acid (131 μl) and red-hot sodium sulfate (2 g) were added thereto. After one hour's stirring at RT, sodium triacetoxyborohydride (759 mg) was added and stirring was carried out for a further two days. For working up, the mixture was concentrated, the residue was suspended in diethyl ether (15 ml), water (10 ml) and 2M HCl (1 ml), further diethyl ether (20 ml) was added, and the organic phase was coarsely separated off. The aqueous phase was first brought to pH 9 with 1M NaOH and extracted with ethyl acetate (3×5 ml), then adjusted to pH 11 and again extracted with ethyl acetate (5×10 ml). The organic extracts were dried and concentrated and the residue was purified by flash chromatography (eluant: MeOH/NEt3 99.5:0.5). 267 mg of the nonpolar diastereomer (m.p. 90-100° C.) were isolated and, dissolved in ethanol/2-butanone (3 ml/15 ml), were converted with 3.3M ethanolic HCl (642 μl) into the corresponding dihydrochloride (white solid; 304 mg; m.p. 215-217° C.).

출처