(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

Base Information

Chemical Name:(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate
CAS No.:1361051-93-5
Molecular Formula:C₃₂H₃₆N₂O₄
Molecular Weight:512.649
Hs Code.:

Synonyms:(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

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Chemical Property of (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

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Technology Process of (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

There total 6 articles about (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-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: 59.0%

: 4894-26-2
3,4-dihydro-β-carboline

: 126378-43-6
(1R,2S,5R)-(-)-8-phenylmenthyl chloroformate

: 171201-21-1
(furan-2-yloxy)triisopropylsilane

: 1361051-93-5
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

: 1361051-91-3
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((R)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

Guidance literature:: 3,4-dihydro-β-carboline; (1R,2S,5R)-(-)-8-phenylmenthyl chloroformate; With 1-butyl-3-methylimidazolium Tetrafluoroborate; In tetrahydrofuran; dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

(furan-2-yloxy)triisopropylsilane; In tetrahydrofuran; dichloromethane; at -78 - -20 ℃; for 12h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0031-1289631

Reference yield:

: 4894-26-2
3,4-dihydro-β-carboline

: 61550-02-5
(furan-2-yloxy)-trimethylsilane

: 126378-43-6
(1R,2S,5R)-(-)-8-phenylmenthyl chloroformate

: 1361051-93-5
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

: 1361051-91-3
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((R)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

Guidance literature:: 3,4-dihydro-β-carboline; (1R,2S,5R)-(-)-8-phenylmenthyl chloroformate; With 1-butyl-3-methylimidazolium Tetrafluoroborate; In tetrahydrofuran; dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

(furan-2-yloxy)-trimethylsilane; In tetrahydrofuran; dichloromethane; at -78 - -20 ℃; for 12h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0031-1289631

Reference yield:

: 6502-82-5
N_b-formyltryptamine

: 1361051-93-5
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((S)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

: 1361051-91-3
(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (R)-1-((R)-2,5-dihydro-5-oxofuran-2-yl)-1,4-dihydro-3H-β-carboline-2(9H)-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: trichlorophosphate / acetonitrile / 3.67 h / 0 °C

1.2: 0 °C

1.3: 0 °C

2.1: 1-butyl-3-methylimidazolium Tetrafluoroborate / tetrahydrofuran; dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 12 h / -78 - -20 °C / Inert atmosphere

With 1-butyl-3-methylimidazolium Tetrafluoroborate; trichlorophosphate; In tetrahydrofuran; dichloromethane; acetonitrile; 1.1: Bischler-Napieralski reaction;
DOI:10.1055/s-0031-1289631