(7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate

Base Information

• Chemical Name: (7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate
• CAS No.: 114907-08-3
• Molecular Formula: C₂₅H₂₃NO₅S
• Molecular Weight: 449.527

Synonyms:(7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate

Chemical Property of (7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate

Chemical Property:

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Technology Process of (7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate

There total 12 articles about (7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-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: 91.0%

(7RS,11SR,12SR)-methyl 9-methyl-6-oxo-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate (114907-07-2) + p-toluenesulfonyl chloride (98-59-9) → (7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate (114907-08-3)

Guidance literature:

With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In benzene; for 0.25h; Ambient temperature;

DOI:10.1021/jo00249a009

Reference yield: 62.0%

(1RS,2SR,3SR)-1-methyl hydrogen 5-methyl-3-(1'-tosylindol-3'-yl)cyclohex-4-ene-1,2-dicarboxylate (131938-86-8) → (7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate (114907-08-3)

Guidance literature:

With PPE; In chloroform; for 0.5h; Heating;

Reference yield:

3-Isoprenylindole (96839-16-6) → (7RS,11SR,12SR)-methyl 9-methyl-6-oxo-5-tosyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate (114907-08-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / benzene / 0.5 h / Ambient temperature

2: 67 percent / BF₃*Et₂O / benzene / 6 h / Ambient temperature

3: 95 percent / sulfuric acid / 24 h / Heating

4: 91 percent / tetra-n-butylammonium hydrogen sulfate, 50percent aq. KOH / benzene / 0.25 h / Ambient temperature

With potassium hydroxide; sulfuric acid; boron trifluoride diethyl etherate; tetra(n-butyl)ammonium hydrogensulfate; In benzene;

DOI:10.1021/jo00249a009

upstream raw materials:

(1RS,2SR,3SR)-1-methyl hydrogen 5-methyl-3-(1'-tosylindol-3'-yl)cyclohex-4-ene-1,2-dicarboxylate

(7RS,11SR,12SR)-methyl 9-methyl-6-oxo-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-octindole-12-carboxylate

p-toluenesulfonyl chloride

3-Isoprenylindole

Downstream raw materials:

C₂₅H₂₅NO₅S

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