((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone

Base Information

Chemical Name:((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone
CAS No.:327983-82-4
Molecular Formula:C₂₄H₂₇N₃O₂
Molecular Weight:389.497
Hs Code.:

Synonyms:((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone

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Chemical Property of ((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone

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Technology Process of ((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone

There total 6 articles about ((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone 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: 95.0%

: 327983-81-3
4-Nitro-benzoic acid (1S,3S)-2-benzyl-3-(pyrrolidine-1-carbonyl)-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl ester

: 327983-82-4
((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; at 55 ℃; for 1h;
DOI:10.1002/1521-3773(20001215)39:24<4521::AID-ANIE4521>3.0.CO;2-M

Reference yield:

: 327983-78-8
[1-(1H-indol-3-ylmethyl)-2-oxo-2-pyrrolidin-1-yl-ethyl]-carbamic acid benzyl ester

: 327983-82-4
((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone

Guidance literature:: Multi-step reaction with 4 steps

1: H₂; aq. AcOH / Pd/C / ethyl acetate

2: 76 percent / NaCNBH₃ / methanol / pH 6

3: 81 percent / toluene / 4 h / Heating

4: 95 percent / aq. NaOH / tetrahydrofuran / 1 h / 55 °C

With sodium hydroxide; hydrogen; sodium cyanoborohydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; 3: Pictet-Spengler reaction;
DOI:10.1002/1521-3773(20001215)39:24<4521::AID-ANIE4521>3.0.CO;2-M

Reference yield:

: 7432-21-5
N-carbobenzyloxy-L-tryptophane

: 327983-82-4
((1S,3S)-2-Benzyl-1-hydroxymethyl-2,3,4,9-tetrahydro-1H-β-carbolin-3-yl)-pyrrolidin-1-yl-methanone

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / NEt₃; HBTU / acetonitrile / 20 °C

2: H₂; aq. AcOH / Pd/C / ethyl acetate

3: 76 percent / NaCNBH₃ / methanol / pH 6

4: 81 percent / toluene / 4 h / Heating

5: 95 percent / aq. NaOH / tetrahydrofuran / 1 h / 55 °C

With sodium hydroxide; hydrogen; sodium cyanoborohydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; acetonitrile; 4: Pictet-Spengler reaction;
DOI:10.1002/1521-3773(20001215)39:24<4521::AID-ANIE4521>3.0.CO;2-M