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Writeup: Lsd synthesis from ergocristine using PyBOP

simplechemistry

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100ml of 10% KOH solution was added to an rbf under inert atmosphere (Ar). This was let to stir and brought up to 75-80C.
5g of ergocristine was added to the flask and the rxn mixture turned yellow as the reaction progressed. The rxn was let to stir for 3 hours and became a homogeneous yellow solution.
The rbf was placed in a freezer and cooled to 6C, acidified to ph3 by drop wise addition of 40% sulfuric acid. White solids immediately precipitated upon addition.
This mixture was let to cool overnight in a freezer and filtered. The solids obtained were washed with et2o, suspended in nh4oh/etoh and insolubles removed by filtration. This was repeated three times.
The colourless filtrate was stripped under high vacuum using a rotovap, dissolved in 1% nh4oh and acidified with 40% sulfuric acid. The precipitated solids were filtered, washed with et2o until free of colour
and dried under vacuum until constant mass. 2g of lysergic acid hydrate was obtained. This was heated under high vacuum until the mass decreased to the stoichiometric anhydrous form. 1.88g, 90% yield

1.88g of lysergic acid hydrate was dissolved in 100ml of DCM in an rbf under an inert atmosphere (Ar). 1.4g of diethylmethylamine was added dropwise slowly. This was let to stir for 15 minutes.
4g of PyBOP was added and the solution was let to stir for another 10 minutes. 0.57g of diethylamine was added and the rxn was let to stir at RT for an hour.
The rxn was quenched using 100ml of 7.5M nh4oh. The DCM layer was pulled, and the aqeuous phase was extracted thrice with DCM. The DCM was stripped under high vacuum at 35C using a rotovap.
The solids leftover were dissolved in ~35ml of cold saturated NaHCO3 and extracted thrice with EtOAc. The organic phase was washed with distilled water, brine and dried with MgSO4.
This was again stripped under high vacuum at 35C using a rotovap until a constant mass. The solids were chromotographed over alumina with 3:1 hexane/dcm.
The collected fraction was stripped under high vacuum and held until constant mass. The iso-lsd was saved for later. 1.99g freebase LSD was obtained.
The solids were dissolved in 8ml of near boiling anhydrous MeOH and 0.464g of anhydrous d-tartaric acid was added. Et2O was added as an anti solvent until cloudiness didn't stop.
This solution was put in a freezer and let to crystallise overnight. The crystalline product was filtered and recrystallised with MeOH three times (until solubility in MeOH is negligible).
2.79g of LSD d-tartate was obtained.
 

HerrHaber

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It would be helpful to state wether this procedure was worked practically (experience tells me that you didn’t imagine the data). Another thing which you should regard as constructive criticism only is for example in the first sentence “10% KOH” asks the question wether “a.q.” or MeOH, using Ar atmosphere with aqueous media is arguably a bias.
 

SchrodingersDogg

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100ml of 10% KOH solution was added to an rbf under inert atmosphere (Ar). This was let to stir and brought up to 75-80C.
5g of ergocristine was added to the flask and the rxn mixture turned yellow as the reaction progressed. The rxn was let to stir for 3 hours and became a homogeneous yellow solution.
The rbf was placed in a freezer and cooled to 6C, acidified to ph3 by drop wise addition of 40% sulfuric acid. White solids immediately precipitated upon addition.
This mixture was let to cool overnight in a freezer and filtered. The solids obtained were washed with et2o, suspended in nh4oh/etoh and insolubles removed by filtration. This was repeated three times.
The colourless filtrate was stripped under high vacuum using a rotovap, dissolved in 1% nh4oh and acidified with 40% sulfuric acid. The precipitated solids were filtered, washed with et2o until free of colour
and dried under vacuum until constant mass. 2g of lysergic acid hydrate was obtained. This was heated under high vacuum until the mass decreased to the stoichiometric anhydrous form. 1.88g, 90% yield
1.88g of lysergic acid hydrate was dissolved in 100ml of DCM in an rbf under an inert atmosphere (Ar). 1.4g of diethylmethylamine was added dropwise slowly. This was let to stir for 15 minutes.
4g of PyBOP was added and the solution was let to stir for another 10 minutes. 0.57g of diethylamine was added and the rxn was let to stir at RT for an hour.
The rxn was quenched using 100ml of 7.5M nh4oh. The DCM layer was pulled, and the aqeuous phase was extracted thrice with DCM. The DCM was stripped under high vacuum at 35C using a rotovap.
The solids leftover were dissolved in ~35ml of cold saturated NaHCO3 and extracted thrice with EtOAc. The organic phase was washed with distilled water, brine and dried with MgSO4.
This was again stripped under high vacuum at 35C using a rotovap until a constant mass. The solids were chromotographed over alumina with 3:1 hexane/dcm.
The collected fraction was stripped under high vacuum and held until constant mass. The iso-lsd was saved for later. 1.99g freebase LSD was obtained.
The solids were dissolved in 8ml of near boiling anhydrous MeOH and 0.464g of anhydrous d-tartaric acid was added. Et2O was added as an anti solvent until cloudiness didn't stop.
This solution was put in a freezer and let to crystallise overnight. The crystalline product was filtered and recrystallised with MeOH three times (until solubility in MeOH is negligible).
2.79g of LSD d-tartate was obtained.
simplechemistry
 
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