trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one

Base Information

• Chemical Name: trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one
• CAS No.: 77306-59-3
• Molecular Formula: C₂₀H₁₈N₂O₄S
• Molecular Weight: 382.44

Synonyms:trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one

Chemical Property of trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one

Chemical Property:

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Technology Process of trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one

There total 3 articles about trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one 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: 52.0%

trans-4-(2-chloroacetamido)-1,3,4,5-tetrahydro-1-(p-tolylsulfonyl)benzindol-5-ol (77291-60-2) → trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one (77306-59-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 0.5h;

DOI:10.1021/jm00357a010

Reference yield:

4-(2-chloroacetamido)-3,4-dihydro-1-(p-tolylsulfonyl)benzindol-5(1H)-one (84056-98-4) → trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one (77306-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaBH₄ / tetrahydrofuran; ethanol / 1 h / Ambient temperature

2: 52 percent / NaH / dimethylformamide / 0.5 h

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00357a010

Reference yield:

4-amino-1,3,4,5-tetrahydro-1-(p-tolylsulphonyl)benzindol-5-one hydrochloride (40380-71-0) → trans-4-(p-tolylsulfonyl)-4,6,6a,7,9,10a-hexahydroindolo<3,4-gh><1,4>benzoxazin-8-one (77306-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / NaHCO₃ / ethyl acetate

2: 95 percent / NaBH₄ / tetrahydrofuran; ethanol / 1 h / Ambient temperature

3: 52 percent / NaH / dimethylformamide / 0.5 h

With sodium tetrahydroborate; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00357a010

upstream raw materials:

trans-4-(2-chloroacetamido)-1,3,4,5-tetrahydro-1-(p-tolylsulfonyl)benzindol-5-ol

4-(2-chloroacetamido)-3,4-dihydro-1-(p-tolylsulfonyl)benzindol-5(1H)-one

4-amino-1,3,4,5-tetrahydro-1-(p-tolylsulphonyl)benzindol-5-one hydrochloride

Downstream raw materials:

(-)-trans-4,6,6a,8,9,10a-hexahydro-7-ethyl-7H-indolo<3,4-gh><1,4>benzoxazine

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