(6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

Base Information

• Chemical Name: (6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole
• CAS No.: 152784-91-3
• Molecular Formula: C₂₃H₂₅NO₂S
• Molecular Weight: 379.523

Synonyms:(6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

Chemical Property of (6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

Chemical Property:

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Technology Process of (6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole

There total 4 articles about (6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole 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: 94.0%

(αξ,6R,8S)-6,8-dimethyl-1-(phenylsulfonyl)-α-propyl-1,6,7,8-tetrahydrocyclopentindole-5-methanol → (6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole (152784-91-3)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Heating;

DOI:10.1016/S0040-4039(00)74096-2

Reference yield:

(6R,8S)-1-(phenylsulfonyl)-5-(hydroxymethyl)-6,8-dimethyl-1,6,7,8-tetrahydrocyclopentindole (152708-69-5) → (6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole (152784-91-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / MnO₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

2: tetrahydrofuran / 0.33 h / -20 °C

3: 94 percent / p-TsOH*H₂O / benzene / 0.5 h / Heating

With manganese(IV) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1248/cpb.42.854

Reference yield:

(6R,8S)-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole-5-carboxaldehyde (152708-70-8) → (6R,8S)-5-<(E)-1-butenyl>-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole (152784-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0.33 h / -20 °C

2: 94 percent / p-TsOH*H₂O / benzene / 0.5 h / Heating

With toluene-4-sulfonic acid; In tetrahydrofuran; benzene;

DOI:10.1248/cpb.42.854

upstream raw materials:

(6R,8S)-1-(phenylsulfonyl)-5-(hydroxymethyl)-6,8-dimethyl-1,6,7,8-tetrahydrocyclopentindole

(6R,8S)-6,8-dimethyl-1-(phenylsulfonyl)-1,6,7,8-tetrahydrocyclopentindole-5-carboxaldehyde

Downstream raw materials:

(6R,8S)-cis-trikentrin B

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