150 mg harmaline (214.268 g/mol) 1 eq. (0.7 mmol)
80 mg NaBH4 (37.83 g/mol) 3 eq. (2.1 mmol)
20 mL MeOH
----
150mg of purified harmalas (harmaline enriched)
[image1]
dissolved in 20mL MeOH, dissolved and set up with mag stirring
[image2]
added 80mg of NaBH4, which evolved vigorous amounts of H2, and an almost instantaneous colour change to a pale yellow, almost colourless solution.
[image3]
TLC (40:10:1) MeOH:EtOAc:10%aqNH3 Left side is starting material harmalas (bottom spot is harmaline, top is harmine) and the right side is post reaction.
After 5 min indicated complete reduction of the harmaline... The spot was colourless compared to the yellow spot of the starting harmalas...
When viewed under 365nm UV light, THH is visible as a weakly fluorescent dark spot with a rf slightly less than that of harmaline.
[image 4]
Very clean reaction, goes 100% in under a minute. I perfer this to zinc just because its so easy and fast and you don't need to deal with zinc salts or use ammonia.
80 mg NaBH4 (37.83 g/mol) 3 eq. (2.1 mmol)
20 mL MeOH
----
150mg of purified harmalas (harmaline enriched)
[image1]
dissolved in 20mL MeOH, dissolved and set up with mag stirring
[image2]
added 80mg of NaBH4, which evolved vigorous amounts of H2, and an almost instantaneous colour change to a pale yellow, almost colourless solution.
[image3]
TLC (40:10:1) MeOH:EtOAc:10%aqNH3 Left side is starting material harmalas (bottom spot is harmaline, top is harmine) and the right side is post reaction.
After 5 min indicated complete reduction of the harmaline... The spot was colourless compared to the yellow spot of the starting harmalas...
When viewed under 365nm UV light, THH is visible as a weakly fluorescent dark spot with a rf slightly less than that of harmaline.
[image 4]
Very clean reaction, goes 100% in under a minute. I perfer this to zinc just because its so easy and fast and you don't need to deal with zinc salts or use ammonia.