Modified Pictet-Spengler reaction and products prepared therefrom

Disclosed is a method of preparing a desired diastereomer of a tetrahydro-beta-carboline having a formula (I) comprising the steps of: (a) TOPviding a tryptophan esterified using an alcohol having a formula R2OH; and (b) reacting the tryptophan ester of step (a) with an aldehyde having a formula R1C...

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Hauptverfasser: DOECKE, CHRISTOPHER WILLIAM, PAWLAK, JOSEPH MATTHEW, ORME, MARK W, MARTINELLI, MICHAEL JOHN, CHELIUS, ERIK
Format: Patent
Sprache:eng
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Zusammenfassung:Disclosed is a method of preparing a desired diastereomer of a tetrahydro-beta-carboline having a formula (I) comprising the steps of: (a) TOPviding a tryptophan esterified using an alcohol having a formula R2OH; and (b) reacting the tryptophan ester of step (a) with an aldehyde having a formula R1CHO to provide the desired diastereomer, wherein the reaction is performed in a solvent in which the desired diastereomer is insoluble and the undesired diastereomer is soluble, wherein R2 is alkyl and R1CHO is an aliphatic or aromatic aldehyde.