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16th August 2012 @ 03:24
Sc: 1-10
Synthesis of SC1-1 from tryptamine and benzaldehyde.

SC1-1 was successfully synthesised (1.389 g, 5.594 mmol, 90.0%, m.p. 119 degrees).

HIRAC


SC1-1 and SC2-1 HIRAC.pdf


Procedure followed:

The synthetic strategy outlined in 'Development of the Pictet-Spengler Reaction Catalyzed by AuCl3/AgOTf' (see reference below) was used in this experiment. Molecular sieves were not used.

SC1-1%20reaction%20scheme.png

16th August 2012
Tryptamine (0.9955 g, 6.213 mmol) and benzaldehyde (9.78 M, 0.67 mL, 6.553 mmol) were combined in dichloromethane (0.2 M, 32 mL). The reaction was stirred at room temperature (23 degrees) for 21 hours.

17th August 2012
Fine light-brown crystals were visible. Solvent was removed on the rotorvap.

20th August 2012
Solid product was harvested as follows: addition and subsequent overnight evaporation of dichloromethane (0.2 M, ~1 mL) was needed to isolate the light brown solid (1.389 g, 5.594 mmol, 90.0%, m.p. 119 degrees). A recrystallisation of crude product in absolute ethanol was prepared (solvent chosen because this gave the best recrystallisation of SC2-1). SC1-1 did not crystalise.

22nd August 2012
NMR analysis was done to confirm the formation of the imine.

Tryptamine starting material:
23.08.12_Tryptamine_1H.pdf

SC1-1 product:
22.08.12_SC1-1_crude_1H.pdf


References:
Youn, S. W. (2006). Development of the Pictet-Spengler Reaction Catalyzed by AuCl3/AgOTf. J. Org. Chem. 71: 2521-2523.

Attached Files
SC1-1 and SC2-1 HIRAC.pdf
SC2-1 reaction scheme.png
SC1-1 reaction scheme.png
Journal of Organic Chemistry_2006.pdf
SC1-1_crude.zip
22.08.12_SC1-1_crude_1H.pdf
Tryptamine.zip
23.08.12_Tryptamine_1H.pdf
2006 supplementary material.pdf
SC1-1.jpg
SC1-1.PNG
11.09.12_SC3-1_column frac 14-23_1H.pdf