5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

Base Information

• Chemical Name: 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole
• CAS No.: 122490-84-0
• Molecular Formula: C₂₃H₂₂N₂O
• Molecular Weight: 342.44

Synonyms:

Chemical Property of 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

Chemical Property:

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Technology Process of 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

There total 6 articles about 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 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: 80.0%

2'-phenylsulfinyl-5-methyl-12-benzyl-6,7,8,9,10,11-hexahydro-oxirano-spiro<2',9>-6,10-imino-5H-cyclooctindole (122490-83-9,122565-45-1,141847-53-2) → 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole (122490-84-0,143120-74-5)

Guidance literature:

With Tributylphosphine oxide; lithium perchlorate; In toluene; for 1h; Heating;

DOI:10.1016/S0040-4020(01)88507-0

Reference yield:

5-methyl-9-hydroxy-9α-chloro-phenylsulfinylmethyl-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (122490-92-0,122565-46-2,141847-52-1) → 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole (122490-84-0,143120-74-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 10 N aq. KOH / tetrahydrofuran / 24 h / Ambient temperature

2: 80 percent / LiClO₄, tri-n-butylphosphine oxide / toluene / 1 h / Heating

With potassium hydroxide; Tributylphosphine oxide; lithium perchlorate; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4020(01)88507-0

Reference yield:

(+/)-5-Methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (22282-00-4,122490-82-8,123806-87-1) → 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole (122490-84-0,143120-74-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) THF, 40 min

2: 85 percent / 10 N aq. KOH / tetrahydrofuran / 24 h / Ambient temperature

3: 80 percent / LiClO₄, tri-n-butylphosphine oxide / toluene / 1 h / Heating

With potassium hydroxide; Tributylphosphine oxide; lithium perchlorate; lithium diisopropyl amide; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4020(01)88507-0

upstream raw materials:

2'-phenylsulfinyl-5-methyl-12-benzyl-6,7,8,9,10,11-hexahydro-oxirano-spiro<2',9>-6,10-imino-5H-cyclooctindole

5-methyl-9-hydroxy-9α-chloro-phenylsulfinylmethyl-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(+/)-5-Methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate

Downstream raw materials:

5-methyl-9-hydroxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

5-methyl-9-butyryloxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

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