(1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

Base Information

Chemical Name:(1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester
CAS No.:655240-18-9
Molecular Formula:C₂₇H₃₂N₂O₅
Molecular Weight:464.561
Hs Code.:

Synonyms:(1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

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Chemical Property of (1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

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Technology Process of (1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

There total 9 articles about (1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester 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: 92.0%

: 13865-19-5
4-oxobutanoic acid methyl ester

: 655240-17-8
2-benzylamino-3-(7-methoxy-1-methyl-1H-indol-3-yl)-propionic acid ethyl ester

: 655240-18-9
(1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

Guidance literature:: 4-oxobutanoic acid methyl ester; 2-benzylamino-3-(7-methoxy-1-methyl-1H-indol-3-yl)-propionic acid ethyl ester; With acetic acid; In dichloromethane; at 0 - 20 ℃;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 168h;
DOI:10.1021/ol0362212

Reference yield:

: 355839-49-5
(2S,5R)-3,6-diethoxy-2-isopropyl-5-[3-(triethylsilyl)prop-2-ynyl]-2,5-dihydropyrazine

: 655240-18-9
(1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / Pd(OAc)2; LiCl; K₂CO₃ / dimethylformamide / 36 h / 100 °C

2: NaH / dimethylformamide / 1.5 h / 0 °C

3: 1.69 g / aq. HCl / tetrahydrofuran / 0 - 20 °C

4: Na₂SO₄ / ethanol / 8 h / 0 °C

5: 8.64 g / NaBH₄; Na₂SO₄ / ethanol / -10 - 20 °C

6: AcOH / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; sodium hydride; potassium carbonate; acetic acid; sodium sulfate; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 6: Pictet-Spengler condensation;
DOI:10.1021/jo052081t

Reference yield:

: 354574-31-5
2-iodo-6-methoxybenzenamine

: 655240-18-9
(1S,3R)-2-Benzyl-8-methoxy-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / Pd(OAc)2; LiCl; K₂CO₃ / dimethylformamide / 36 h / 100 °C

2: NaH / dimethylformamide / 1.5 h / 0 °C

3: 1.69 g / aq. HCl / tetrahydrofuran / 0 - 20 °C

4: Na₂SO₄ / ethanol / 8 h / 0 °C

5: 8.64 g / NaBH₄; Na₂SO₄ / ethanol / -10 - 20 °C

6: AcOH / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; sodium hydride; potassium carbonate; acetic acid; sodium sulfate; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 6: Pictet-Spengler condensation;
DOI:10.1021/jo052081t