Tryptamine (1 g, 6.24 mmol, 1.0 eq) was dissolved in 40 mL
ice-cold methanol, followed by the addition of glacial acetic acid
(1.26 g, 21.0 mmol, 1.20 mL, 3.4 eq), sodium cyanoborohydride
(629 mg, 10.0 mmol, 1.6 eq), and left to stir on ice for 5 min. An
aqueous solution of 39% (w/v) formaldehyde (429 mg, 14.3 mmol,
1.1 mL, 2.3 eq) in 10 mL methanol was added dropwise to the
reaction mixture over a period of 20 min. The ice was removed
and the reaction was left to stir for 2.5 h at room temperature.
NaOH (3 mL, 20%) was added and the solvent was removed under
reduced pressure. This was followed by the addition of 20 mL
distilled water and three extractions with 20 mL chloroform.
The combined organic layers were washed once with 20 mL
water and 20 mL brine, dried with MgSO4, and ?ltered. The ?lter
cake was washed twice with 20 mL chloroform with the ?ltrate
evaporated under reduced pressure. The oily residue was dried
over P2O5 overnight to yield 1.169 g of a pale brown waxy solid and
characterized by GC-MS analysis. The standard conditions were
then modi?ed to study the impact of varied reagent stoichiometry
(Table 1). All reactions were carried out in duplicate

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