28383-23-5Relevant articles and documents
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Hoffmann et al.
, p. 1557,1563,1570 (1959)
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Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: Synthesis of psilocin, bufotenin, and serotonin
Bartolucci, Silvia,Mari, Michele,Di Gregorio, Giovanni,Piersanti, Giovanni
, p. 2233 - 2238 (2016/04/19)
Observations concerning the synthesis of substituted tryptamine derivatives starting from indoles and 1,n-amino alcohols via the borrowing hydrogen process are discussed. This catalytic, single-step, and modular approach to tryptamines and homotryptamines allows the synthesis of branched and nonbranched tryptamines as well as tryptamine-based natural products such as psilocin, bufotenin, and serotonin.
Improvements to the synthesis of psilocybin and a facile method for preparing the O-acetyl prodrug of psilocin
Nichols, David E.,Frescas, Stewart
, p. 935 - 938 (2007/10/03)
An improved procedure to accomplish the O-phosphorylation of 4-hydroxy- N,N-dimethyltryptamine (psilocin 5) is reported that utilizes reaction between the O-lithium salt of 5 and tetra-O-benzylpyrophosphate. The O- benzyl groups were removed by catalytic hydrogenation over palladium on carbon to afford N,N-dimethyl-4-phosphoryloxytryptamine (psilocybin, 1). In view of difficulties encountered in the preparation of 1, it is suggested that 4-acetoxy-N,N-dimethyltryptamine (2) may be a useful alternative for pharmacological studies. The latter was obtained following catalytic O- debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.