(3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.0^3,8]decan-3-ol

Base Information

• Chemical Name: (3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.0^3,8]decan-3-ol
• CAS No.: 159979-25-6
• Molecular Formula: C₂₇H₃₂N₂O₄S
• Molecular Weight: 480.628

Synonyms:(3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.0^3,8]decan-3-ol

Chemical Property of (3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.0^3,8]decan-3-ol

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Technology Process of (3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.0^3,8]decan-3-ol

There total 5 articles about (3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.0^3,8]decan-3-ol 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: 85.0%

Methanesulfonic acid (1S,4R,5R,6S)-6-hydroxy-4-[1-(4-methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-3-aza-bicyclo[3.3.1]non-6-ylmethyl ester (159979-23-4) → (3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.03,8]decan-3-ol (159979-25-6)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1016/S0957-4166(00)86278-3

Reference yield:

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.03,8]decan-3-ol (159979-25-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Hg(NO₃)2, 2.) 1N aq. NaOH, NaBH₄, 3.) 18percent aq. HCl

2: 1.) NaH / 1.) THF, 0 deg C, 2 h, 2.) THF, 25 deg C, 16 h

3: 3 percent / N-methylmorpholine N-oxide, OsO₄ / dioxane; H₂O / 48 h / 25 °C

4: 91 percent / pyridine / CH₂Cl₂ / 5 h / 25 °C

5: 85 percent / Et₃N / CH₂Cl₂ / 12 h / 25 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; sodium hydride; mercury(II) nitrate; 4-methylmorpholine N-oxide; triethylamine; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/S0957-4166(00)86278-3

Reference yield:

(+)-makomakine (79559-56-1) → (3S,6S,8R,9R)-9-[1-(4-Methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-10,10-dimethyl-1-aza-tricyclo[4.3.1.03,8]decan-3-ol (159979-25-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, 0 deg C, 2 h, 2.) THF, 25 deg C, 16 h

2: 3 percent / N-methylmorpholine N-oxide, OsO₄ / dioxane; H₂O / 48 h / 25 °C

3: 91 percent / pyridine / CH₂Cl₂ / 5 h / 25 °C

4: 85 percent / Et₃N / CH₂Cl₂ / 12 h / 25 °C

With pyridine; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/S0957-4166(00)86278-3

upstream raw materials:

Methanesulfonic acid (1S,4R,5R,6S)-6-hydroxy-4-[1-(4-methoxy-benzenesulfonyl)-1H-indol-3-ylmethyl]-2,2-dimethyl-3-aza-bicyclo[3.3.1]non-6-ylmethyl ester

beta-pinene

(+)-makomakine

N⁽¹⁾-p-methoxyphenylsulfonylmakomakine

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