(1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Base Information

Chemical Name:(1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
CAS No.:1353844-73-1
Molecular Formula:C₃₃H₂₆N₂O₆
Molecular Weight:546.579
Hs Code.:

Synonyms:(1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

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Chemical Property of (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

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Technology Process of (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

There total 3 articles about (1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

: 54917-85-0
3,4-dibenzoyloxybenzaldehyde

: L-tryptophan methyl ester hydrobromide

: 1353844-73-1
(1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Guidance literature:: 3,4-dibenzoyloxybenzaldehyde; L-tryptophan methyl ester hydrobromide; In isopropyl alcohol; for 2h; Reflux;

In nitromethane; toluene; for 36h; optical yield given as %de; diastereoselective reaction; Reflux;
DOI:10.1016/j.tetasy.2011.10.011

Reference yield: 90.0%

: 54917-85-0
3,4-dibenzoyloxybenzaldehyde

: 7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8
(S)-tryptophan methyl ester hydrochloride

: 1353844-73-1
(1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Guidance literature:: 3,4-dibenzoyloxybenzaldehyde; (S)-tryptophan methyl ester hydrochloride; In isopropyl alcohol; for 2h; Reflux;

In nitromethane; toluene; for 48h; optical yield given as %de; diastereoselective reaction; Reflux;
DOI:10.1016/j.tetasy.2011.10.011

Reference yield:

: 4299-70-1
L-tryptophan methyl ester

: 1353844-73-1
(1R,3S)-methyl 1-(3,4-dibenzoyloxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen bromide / ethyl acetate / 1.25 h / 0 °C

2.1: isopropyl alcohol / 2 h / Reflux

2.2: 36 h / Reflux

With hydrogen bromide; In ethyl acetate; isopropyl alcohol; 2.1: Pictet-Spengler reaction;
DOI:10.1016/j.tetasy.2011.10.011