1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, methyl ester, (1R,3S)-

Base Information

• Chemical Name: 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, methyl ester, (1R,3S)-
• CAS No.: 391869-93-5
• Molecular Formula: C₂₁H₂₂N₂O₃S
• Molecular Weight: 382.483
• Mol file: 391869-93-5.mol

Synonyms:

Chemical Property of 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, methyl ester, (1R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, methyl ester, (1R,3S)-

There total 3 articles about 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-[[(R)-(4-methylphenyl)sulfinyl]methyl]-, methyl ester, (1R,3S)- 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: 35.0%

L-tryptophan methyl ester (4299-70-1) + 4,4,6-Trimethyl-2-((R)-toluene-4-sulfinylmethyl)-[1,3]oxazinane (391869-91-3) → (cis,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (391869-93-5) + (trans,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (391869-94-6)

Guidance literature:

With acetic acid; In acetonitrile; for 10h; Heating;

DOI:10.1016/j.tet.2004.07.062

Reference yield:

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) → (cis,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (391869-93-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 84 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

2.1: 100 percent / NaBH₄; HCl / ethanol; tetrahydrofuran; H₂O / 1 h / -45 °C / pH 7 - 8

3.1: 35 percent / AcOH / acetonitrile / 10 h / Heating

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; acetic acid; In tetrahydrofuran; ethanol; hexane; water; acetonitrile;

DOI:10.1016/j.tet.2004.07.062

Reference yield:

4,4,6-trimethyl-2-(toluene-4-sulfinylmethyl)-5,6-dihydro-4H-[1,3]oxazine (391869-90-2) → (cis,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (391869-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaBH₄; HCl / ethanol; tetrahydrofuran; H₂O / 1 h / -45 °C / pH 7 - 8

2: 35 percent / AcOH / acetonitrile / 10 h / Heating

With hydrogenchloride; sodium tetrahydroborate; acetic acid; In tetrahydrofuran; ethanol; water; acetonitrile;

DOI:10.1016/j.tet.2004.07.062

upstream raw materials:

L-tryptophan methyl ester

4,4,6-Trimethyl-2-((R)-toluene-4-sulfinylmethyl)-[1,3]oxazinane

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

4,4,6-trimethyl-2-(toluene-4-sulfinylmethyl)-5,6-dihydro-4H-[1,3]oxazine