(6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate

Base Information

• Chemical Name: (6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate
• CAS No.: 147991-91-1
• Molecular Formula: C₂₄H₂₁F₃N₂O₅S
• Molecular Weight: 506.502

Synonyms:(6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate

Chemical Property of (6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of (6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate

There total 7 articles about (6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-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: 53.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (-)-(6S,10S)-benzyl 5-methyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-12-carboxylate (136612-38-9,148022-34-8) → (6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate (147991-91-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 2h; Ambient temperature;

Reference yield:

(3S)-methyl 1-(2-methoxycarbonylethyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate (126366-08-3,136612-30-1) → (6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate (147991-91-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / NaHCO₃ / CH₂Cl₂ / 4 h / Ambient temperature

2: 82 percent / NaH / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 30 min

3: 70 percent / NaH, MeOH / dimethylformamide / 5 h / Ambient temperature

4: 73 percent / NaCl / H₂O; dimethylformamide / 6 h / 130 °C

5: 53 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

With methanol; sodium hydride; sodium hydrogencarbonate; sodium chloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

(1S,3S)-2-benzyl 3-methyl 1-(2-methoxycarbonylethyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-2,3-dicarboxylate (136612-34-5) → (6S,10S)-benzyl 5-methyl-9-trifluoromethylsulphonyloxy-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate (147991-91-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / NaH, MeOH / dimethylformamide / 5 h / Ambient temperature

2: 73 percent / NaCl / H₂O; dimethylformamide / 6 h / 130 °C

3: 53 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

With methanol; sodium hydride; sodium chloride; In tetrahydrofuran; water; N,N-dimethyl-formamide;

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

(-)-(6S,10S)-benzyl 5-methyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-12-carboxylate

(3S)-methyl 1-(2-methoxycarbonylethyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate

(6S,10S)-12-benzyl 8-methyl 5-methyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8,12-dicarboxylate

Downstream raw materials:

(6S,10S)-benzyl 9-cyano-5-methyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-carboxylate

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