반응 #92664

반응 방정식

5,6α-epoxicholestan-3β-ol

tryptamine

1-Butanol

→

5α-Hydroxy-6β-(3-propylamino)-cholestan-3β-ol

수율 71.5%

용매

methyl-tertbutyl-ether

반응 조건

후처리

1. 1
   기타equipped with a magnetic stirrer bar
2. 2
   온도the mixture heated
3. 3
   온도to reflux for 40 h
4. 4
   세척washed with water (5 vol) and with brine (5 vol)
5. 5
   세척eluted with methyl-tertbutyl-ether (3 vol)
6. 6
   기타the solvent was removed under reduced pressure

실험 절차

5,6α-epoxicholestan-3β-ol (8.9 g, 22.1 mmol, 1 eq) and tryptamine (7.1 g, 44.1 mmol, 2 eq) were charged in a round-bottomed flask equipped with a magnetic stirrer bar. 1-Butanol (70 ml, 5 vol) was added and the mixture heated to reflux for 40 h. The reaction mixture was cooled at r.t., diluted with methyl-tertbutyl-ether (5 vol) and washed with water (5 vol) and with brine (5 vol). The organic layer was passed through a silica pad (40 g) eluted with methyl-tertbutyl-ether (3 vol) then 10% Methanol/ethyl acetate (60 vol). Fractions of interest were pooled and the solvent was removed under reduced pressure to give 5α-Hydroxy-6β-(3-propylamino)-cholestan-3β-ol as a white solid (7.3 g, 59%). In same conditions, use of ethanol as solvent (40 vol) and Ca(OTf)2 as catalyst gave a 21% yield.

출처